簡易檢索 / 詳目顯示

研究生: 藍密司
Ramesh B. Dateer
論文名稱: Gold-Catalyzed New Organic Transformations Involving Activation of C-C Triple Bond for the Synthesis of N and O Containing Molecules
金催化活性碳-碳三鍵, 以新的有機轉化方式合成含氮與氧的分子
指導教授: 劉瑞雄
口試委員: 劉瑞雄
鄭建鴻
蔡易州
孫仲銘
侯敦仁
學位類別: 博士
Doctor
系所名稱: 理學院 - 化學系
Department of Chemistry
論文出版年: 2013
畢業學年度: 101
語文別: 英文
論文頁數: 509
中文關鍵詞: 催化胺炔類環化加成反應
相關次數: 點閱:2下載:0
分享至:
查詢本校圖書館目錄 查詢臺灣博碩士論文知識加值系統 勘誤回報
  • ABSTRACT
    .
    本文介紹了過渡金屬催化的新發展,以有機轉化合成含氮與氧的環化或非環化合物,依據轉化的類型,本篇論文分為五個章節.
    第一章節描述用金催化1-氨基-2-芳基-1-炔類與烯烃類化合物,行分子間{4+2}環化加成.此反應會形成gold carbenoid型式的中間體,並適用於多種電子密度高的烯烃類以及芳香族和雜環類炔醯胺. 炔醯胺化學在近十年被高度探討,因為它的穩定性與反應性,且開啟了通往新立體選擇與分子內反應的大門,此在傳統的炔醯胺是不可能的.
    第二章描述用金催化氨炔類化合物行1,2-雙官能基轉化,藉一外部的氧化劑行一鍋化反應產生1,2-氨醇. 1,2-雙官能基轉化在烯類常見,但很少見在炔類.此一鍋化合成1,2-氨醇,突顯新催化的重要性.
    第三章節描述金屬催化3-烯-1-炔醯胺,行[4+1]環化加成反應以合成2-氨呋喃, 在金屬幫助下環化加成1,3共振化合物與小分子,發現在有機合成具有廣泛的應用性, 呋喃衍生物由3-烯-1-炔醯胺與外加氧化劑合成而得,突顯新催化的重要性.
    第四章描述一價金催化炔基酯,以串聯分子間[3+2]環化加成反應可高效合成高度官能基化的2,3-二氫呋喃.再多種雜環化合物中, 二氫呋喃衍生物被廣泛研究,因為其為許多天然物的重要亞基.
    第五章描述一價金催化3-烯-1-炔二氧化噻嗪行oxoamination,用硝酮當外部氧化劑.高效合成大範圍的oxoamination衍生物的方法被開發出來。


    Contents page Acknowledgement III Abstract V List of Schemes VII List of Tables X List of Figures XI List of Publications XII Abbreviations XIII Chapter I: Gold- Catalyzed Intermolecular [4+2] - Cycloaddition of Ynamides with Alkenes Introduction 2 Results and Discussion 11 Conclusions 19 Experimental Procedures 19 Spectral Data of key compounds 21 References 36 Chapter II: Gold-Catalyzed 1, 2-Difunctionalizations of Aminoalkynes Using Nitroso Arenes Introduction 41 Results and Discussion 50 Conclusions 56 Experimental Procedures 56 Spectral Data of key compounds 57 References 68 Chapter III: Gold-catalyzed synthesis of substituted 2-aminofurans via formal [4+1]- cycloadditions on 3-en-1-ynamides II Introduction 73 Results and Discussion 79 Conclusions 88 Experimental Procedures 88 Spectral Data of key compounds 91 References 104 Chapter IV: Gold(I)-Catalyzed Tandem Intermolecular [3+2]-Cycloaddition of Alkynyl Ester:An Atom Economic Approach for the Efficient Synthesis of Highly Functionalized 2,3 Dihydrofurans Introduction 116 Results and Discussion 119 Conclusions 126 Experimental Procedures 126 Spectral Data of key compounds 127 References 138 Chapter V: Gold(I)-Catalyzed Oxoamination of 3-en-1-ynthiazinedioxide Using Nitrone as a External Oxidant Introduction 144 Results and Discussion 151 Conclusions 161 Experimental Procedures 161 Spectral Data of key compounds 164 References 173 X-Ray Crystal Data and 1H & 13C NMR Spectras 175

    (1) a) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed., 2005, 44, 4442. b)
    Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed, 2005, 44, 4490.
    (2) a) Trost, B. M. Acc. Chem. Res. 2002, 35, 695. b) Trost, B. M. Angew Chem. Int. Ed. Engl.
    1995, 34, 259. c) Trost, B. M. Science 1991, 254, 1471.
    (3) a) Anastas, P.; Warner, J. C. in Green Chemistry, Theory and Practice, Oxford University
    Press, Oxford, 1998. b) Anastas, P. T.; Kirchhoff, M. M. Acc. Chem. Res. 2002, 35, 686. c)
    Anastas, P. T.; Zimmerman, J. B. Environ. Sci. Technol. 2003, 37, 94A. d) Poliakoff, M.;
    Fitzpatrick, J. M.; Farren, T. R.; Anastas, P. T. Science 2002, 297, 807. e) Trost, B. M.; Toste,
    D. F.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067.
    (4) a) Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127. b) Ojima, I.; Tzamarioudaki,
    M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635. c) Lautens, M.; Klute, W.; Tam, W. Chem.
    Rev. 1996, 96, 49.
    (5) a) Jiménez-Núñez, E.; Echavarren, A. M. Chem. Rev. 2008, 108, 3326. b) Gorin, D. J.; Sherry,
    B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351. c) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180.
    d) Fürstner, A.; Davies, P. W. Angew. Chem. Int. Ed. 2007, 46, 3410. e) Patil, N. T.; Yamamoto,
    37
    Y. Chem. Rev. 2008, 108, 3395. f) Sohel, S. M. A.; Liu, R.-S. Chem. Soc. Rev. 2009, 38, 2269. g) López, F.; Mascareńas, J. L. Beilstein, J. Org. Chem. 2011, 7, 1075.
    (6) For reviews see; Hashmi, A. S. K.; Rudolph, M. Chem. Soc. Rev. 2008, 37, 1766.
    (7) a) Marion, F.; Coulomb, J.; Courillon, C.; Fensterbank, L.; Malacria, M. Org. Lett. 2004, 6, 1509. b) Marion, F.; Coulomb, J.; Servais, A.; Courillon, C.; Fensterbank, L.; Malacria, M. Tetrahedron 2006, 62, 3856. c) Nieto-Oberhuber, C; Lupez, S; MuMoz, M. P.; BuMuel, E.; Nevado, C.; Echavarren, A. M. Angew. Chem. Int. Ed. 2005, 44, 6146. d) Nevado, C.; Cqrdenas, D. J.; Echavarren, A. M.; Chem. Eur. J. 2003, 9, 2627.
    (8) a) Jiménez-Núñez, E.; Molawi, K.; Echavarren, A. M. Chem. Commun. 2009, 7327. b) Molawi, K.; Delpont, N.; Echavarren, A. M. Angew. Chem. 2010, 122, 3595; Angew.Chem. Int. Ed. 2010, 49, 3517. c) Fürstner, A.; Hannen, P. Chem. Eur. J. 2006, 12, 3006. d) Fürstner, A.; Hannen, P. Chem. Commun. 2004, 2546. e) Linghu, X.; Kennedy-Smith, J. J.; Toste, F. D. Angew. Chem. Int. Ed. 2007, 46, 7671. f) Hashmi, A. S. K.; Ding, L.; Bats, J. W.; Fisher, P.; Frey, W. Chem. Eur. J. 2003, 9, 4339. g) Couty, S.; Meyer, C.; Cossy, J. Angew.Chem. Int. Ed. 2006, 45, 6726.
    (9) Ho, T.-L.; Lee, K.-Y.; Chen, C.-K. J. Org. Chem. 1997, 62, 3365.
    (10) Ma, X.; Gang, D. R.; Nat. Prod. Rep. 2004, 21, 752.
    (11) For a review on organocatalysis in the synthesis of natural products, see: Marcia de Figueiredo, R.; Christmann, M. Eur. J. Org. Chem. 2007, 2575.
    (12) Ratnayake, R.; Covell, D.; Ransom, T. T.; Gustafson, K. R.; Beutler, J. A. Org. Lett. 2009, 11, 57.
    (13) a) Hashmi, A. S. K.; Blanco, M. C.; Kurpejovic, E.; Frey, W.; Bats, J. W. Adv. Synth. Catal, 2006, 348, 709. b) Bayler, A.; Bauer, A.; Schmidbaur, H. Chem. Ber./Recueil 1997, 130, 115.
    (14) López-Carrillo, V.; Echavarren, A. M. J. Am. Chem. Soc. 2010, 132, 9292.
    (15) a) Jiménez-Núñez, E.; Echavarren, A. M. Chem. Rev. 2008, 108, 3326. b) Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351. c) Michelet, V.; Toullec, P. Y.; Genȇt, J.-P. Angew. Chem.,Int. Ed. 2008, 47, 4268. d) Lee, S. I.; Chatani, N. Chem. Commun.2009, 371. e) Fürstner, A. Chem. Soc. Rev. 2009, 38, 3208. f) Nieto-Oberhuber, C.; Muñoz, M. P.; Buñuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402. g) Nieto-Oberhuber, C.; López, S.; Muñoz, M. P.; Cárdenas, D. J.; Bunuel, E.; Nevado, C.; Echavarren, A. M. Angew. Chem., Int. Ed. 2005, 44, 6146.
    38
    (16) a) Fürstner, A.; Szillat, H.; Stelzer, F. J. Am. Chem. Soc. 2000, 122, 6785. b) Fürstner, A.; Stelzer, F.; Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863. c) Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305.
    (17) a) Böhringer, S.; Gagosz, F. Adv. Synth. Catal. 2008, 350, 2617. b) Trost, B. M.; Tanoury, G. J. J. Am. Chem. Soc. 1988, 110, 1636. c) Marion, F.; Coulomb, J.; Courillon, C.; Fensterbank, L.; Malacria, M. Org. Lett. 2004, 6, 1509. d) Fürstner, A.; Davies, P. W.; Gress, T. J. Am. Chem. Soc. 2005, 127, 8244. e) Nieto-Oberhuber, C.; Pérez-Galán, P.; Herrero-Gómez, E.; Lauterbach, T.; Rodrıguez, C.; López, S.; Bour, C.; Rosellón, A.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2008, 130, 269. f) Brown, T. J.; Dickens, M. G.; Widenhoefer, R. A. J. Am. Chem. Soc. 2009, 131, 6350. g) Brown, T. J.; Dickens, M. G.; Widenhoefer, R. A. Chem. Commun. 2009, 6451. h) Urbano, J.; Hormigo, A. J.; de Frémont, P.; Nolan, S. P.; Dıáz-Requejo, M. M.; Pérez, P. J. Chem. Commun. 2008, 759.
    (18) For chemistry of ynamides, see: a) DeKorver, K. A.; Li, H.; Lohse, A. G.; Hayashi, R.; Lu, Z.; Zhang, Y.; Hsung, R. P.; Chem. Rev. 2010, 110, 5064. b) Evano, G.; Coste, A.; Jouvin, K. Angew. Chem. Int. Ed. 2010, 49, 2840. c) Hashmi, A. S. K.; Rudolph, M.; Huck, J.; Frey, W.; Bats, J. W.; Hamzić, M. Angew. Chem. 2009, 121, 5962; Angew. Chem. Int. Ed. 2009, 48, 5848.
    (19) For gold-catalyzed electrophilic activation of ynamides, see: a) Li, C.-W.; Pati, K.; Lin, G.-Y.; Abu Sohel, S. M.; Hung, S. H.-H.; Liu, R.-S. Angew. Chem. 2010, 122, 10087. Angew. Chem. Int. Ed. 2010, 49, 9891. b) Davies, P. W.; Cremonesi, A.; Martin, N.; Chem. Commun. 2011, 47, 379. c) Li, C.; Zhang, L.; Org. Lett. 2011, 13, 1738. d) Vasu, D.; Hung, H. H.; Bhunia, S.; Das, A.; S. Gawade.; Liu, R.-S. Angew. Chem. 2011, 123, 7043; Angew. Chem. Int. Ed. 2011, 50, 6911. e) Kramer, S.; Odabachian, Y.; Overgaard, J.; Rottander, M.; Gagosz, F.; Skrydstrup, T. Angew. Chem. 2011, 123, 5196; Angew. Chem. Int. Ed. 2011, 50, 5090. f) Hashmi, A. S. K.; Bührle, M.; Wőlfle, M.; Rudolph, M.; Wieteck, M.; Rominger, F.; Frey, W.; Chem. Eur. J. 2010, 16, 9846. g) Davies, P. W.; Cremonesi, A.; Dumitrescu, L. Angew. Chem. Int. Ed. 2011, 50, 8931.
    (20) For [3+2]-cycloadditions of ynamides, see a) Zhang, X.; Hsung, R. P.; You, L. Org. Biomol. Chem. 2006, 4, 2679. b) Ijsselstijn, M.; Cintrat, J. -C. Tetrahedron, 2006, 62, 3837.
    (21) a) Zificsak, C. A.; Mulder, J. A.; Rameshkumar, C.; Wei, L.-L.; Hsung, R. P. Tetrahedron 2001, 57, 7575. b) Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P. Synlett 2003, 1379. c) Katritzky, A. R.; Jiang, R.; Singh, S. K. Heterocycles 2004, 63, 1455.
    39
    (22) a) Katritzky, A. R.; Singh, S. K.; Jiang, R. Tetrahedron 2006, 63, 3794. b) Nadipuram, A. K.; Kerwin, S. M. Tetrahedron 2006, 63, 3798. c) Ishihara, T.; Mantani, T.; Konno, T.; Yamanaka, H. Tetrahedron 2006, 63, 3783. d) Murch, P.; Williamson, B. L.; Stang, P. J. Synthesis 1994, 1255.
    (23) a) Riddell, N.; Villeneuve, K.; Tam, W.; Org. Lett. 2005, 7, 3681 b) Villeneuve, K.; Riddell, N.; Tam. W.; Tetrahedron 2006, 62, 3823.
    (24) Kohnen, A. L.; Mak, X. Y.; Lam, T. Y.; Dunetz, J. R.; Danheiser, R. L. Tetrahedron 2006, 62, 3815.
    (25) a) Zhang, X.; Hsung, R. P.; You, L. Org. Biomol. Chem. 2006, 4, 2679. b) IJsselstijn, M.; Cintrat, J.-C. Tetrahedron 2006, 62, 3837.
    (26) a) Zhang, X.; Li, H.; You, L.; Tang, Y.; Hsung, R. P. Adv. Synth.Catal. 2006, 348, 2437. b) Zhang, X.; Hsung, R. P.; Li, H. Chem. Commun. 2007, 2420. c) Kim, J. Y.; Kim, S. H.; Chang, S. Tetrahedron Lett. 2008, 49, 1745. d) Oppilliart, S.; Mousseau, G.; Zhang, L.; Jia, G.; Thury, P.; Rousseau, B.; Cintrat, J.-C. Tetrahedron 2007, 63, 8094.
    (27) a) Oppenheimer, J.; Johnson, W. L.; Tracey, M. R.; Hsung, R. P.; Yao, P.-Y.; Liu, R.; Zhao, K. Org. Lett. 2007, 9, 2361. b) Goffin, E.; Legrand, Y.; Viehe, H. G. J. Chem. Res., Synop. 1977, 105.
    (28) a) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1998, 37, 489. b) Ogoshi, S.; Nishimura, A.; Ohashi, M. Org. Lett. 2010, 12, 3450.
    (29) a) Nieto-Oberhuber, C.; López, S.; Echavarren, A. M. J. Am. Chem. Soc. 2005, 127, 6178. b) Nieto-Oberhuber, C.; Pérez-Galán, P.; Herrero-Gómez, E.; Lauterbauch, T.; Rodriguez, C.; López, S.; Bour, C.; Rosellón, A.; Cárdenas, D. J; Echavarren, A. M. J. Am. Chem. Soc. 2008, 130, 269 c) Faustino, H.; López, F.; Castedo, L.; Mascareńas, J. L.; Chem. Sci. 2011, 2, 633.
    (30) DeKorver, K.A.; Hsung, R.P; Lohse, A.G, Zhang, Y. Org. Lett. 2010, 12, 1840.
    (1) (a) Kishi, Y. Pure Appl. Chem. 1993, 65, 771. (b) Suh, E. M.; Kishi, Y. J. Am. Chem. Soc. 1994, 116.
    (2) (a) Tietze, L. F.; Beifuss, U. Angew.Chem., Int. Ed. Engl. 1993, 32, 131. (b) Tietze, L. F. Chem. Ind. 1995, 453. (c) Waldmann, H. “Domino Reaction” in Organic Synthesis Highlight II; Waldmann, H., Ed.; VCH: Weinheim, 1995; pp 193-202. (d) Hall, N. Science 1994, 32, 266.
    (3) For general reviews, see: (a) Ho, T.-L. Tactics of Organic Synthesis; Wiley-Interscience: New York, 1994; p 79. (b) Tietze, L. F. Chem. Rev. 1996, 96, 115. (c) Winkler, J. D. Chem. Rev. 1996, 96,167. (d) Denmark, S. E. Thorarensen, A. Chem. Rev. 1996, 96, 137.
    (4) Reviews for gold catalysis: (a) Das, A.; Abu, S. M. A.; Liu, R. S.Org. Biomol. Chem. 2010, 8, 960. (b) Sohel, S. M. A.; Liu, R.-S. Chem. Soc. Rev 2009, 38, 2269. (c) Arcadi, A. Chem. Rev. 2008, 108, 3266. (d) Jiménez-Núñez, E.; Echavarren, A. M. Chem. Rev. 2008, 108, 3326. (e) Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351. (f) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180.
    (5) Xu, C.-F.; Xu, M.; Jia, Y.-X.; Li, C.-Y. Org. Lett. 2011, 13, 1556.
    (6) (a) Rozwadowska, M. D.; Chrzanowska, M. Tetrahedron 1985, 41, 2885. (b) Angelstro, M. R.; Mehdi, S.; Burkhart, J. P.; Peet, N. P.; Bey, P. J. Med. Chem. 1990, 33, 11. (c) Maurya, R.; Singh, R.; Deepak, M.; Handa, S. S.; Yadav, P. P.; Mishra, P. K. Phytochemistry 2004, 65, 915. (d) Mahabusarakam, W.; Deachathai, S.; Phongpaichit, S.; Jansakul, C.; Taylor, W. C. Phytochemistry 2004, 65, 1185. (e) Nicolaou, K. C.; Gray, D. L. F.; Tae, J. J. Am. Chem. Soc. 2004, 126, 613. (f) Wadkins, R. M.; Hyatt, J. L.; Wei, X.; Yoon, K. J. P.; Wierdl, M.; Edwards, C. C.; Morton, C. L.; Obenauer, J. C.; Damodaran, K.; Beroza, P.; Danks, M. K.; Potter, P. M. J. Med. Chem. 2005, 48, 2906.
    (7) For recent reviews on synthesis and reaction of ynamides, see: (a) Evano, G.; Coste, A.; Jouvin, K. Angew. Chem., Int. Ed. 2010, 49, 2840. (b) DeKorver, K. A.; Li, H.; Lohse, A. G.; Hayashi, R.; Lu, Z.; Zhang, Y.; Hsung, R. P. Chem. Rev. 2010, 110, 5064. c) Evano, G.; Coste, A.; Jouvin, K. Angew. Chem., Int. Ed. 2010, 49, 2840. d) He, W.; Li, C.; Zhang, L. J. Am. Chem. Soc. 2011, 133, 8482.
    (8) Recent review for α-carbonyl gold carbenoids: Xiao, J.; Li, X. Angew. Chem., Int. Ed. 2011, 50, 7226.
    69
    (9) Gold-catalyzed alkyne oxidations using external oxidants to give enones and four- membered heterocycles: (a) Ye, L.; Cui, L.; Zhang, G.; Zhang, L. J. Am. Chem. Soc. 2010, 132, 3258. (b) Ye, L.; He, W.; Zhang, L. J. Am. Chem. Soc. 2010, 132, 8550. (c) Ye, L.; He, W.; Zhang, L. Angew. Chem. Int. Ed. 2011, 50, 3236. (d) Vasu, D.; Hung, H.-H.; Bhunia, S.; Gawade, S. A.; Das, A.; Liu, R.-S. Angew Chem Int. Ed. 2011, 50, 6911.
    (10) For monographs, see: (a) Dorwald, F. Z. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, Germany, 1999. (b) Barluenga, J.; Rodrıǵuez, F.; Fanãnaś, F. J.; Floѓez, J. In Metal Carbenes in Organic Synthesis; Doötz, K. H., Ed.; Topics in Organometallic Chemistry, Vol. 13; Springer: Berlin, 2004; pp 59-122. (c) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides; Wiley: New York, 1998.)
    (11) Gold-catalyzed oxidation of aminoalkynes: (a) Li, C.-W.; Pati, K.; Lin, G.-Y.; Abu Sohel, S. M.; Hung, H.-H.; Liu, R.-S. Angew. Chem., Int. Ed. 2010, 49, 9891. (b) Davies, P. W.; Cremonesi, A.; Martin, N. Chem. Commun. 2011, 47, 379. (c) Li, C.; Zhang, L. Org. Lett. 2011, 13, 1738.
    (12) For selected reviews, see: (a) Fürstner, A.; Davies, P. W. Angew. Chem Int. Ed. 2007, 46, 3410. (b) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180. (c) Shen, H. C. Tetrahedron 2008, 64, 3885. (d) Skouta, R.; Li, C.-J. Tetrahedron 2008, 64, 4917. (e) Muzart, J. Tetrahedron 2008, 64, 5815. (f) Li, Z.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239. (g) Arcadi, A. Chem. Rev. 2008, 108, 3266. (h) Jiménez-Núñez.; Echavarren, A. M. Chem. Rev. 2008, 108, 3326. (i) Gorin, D. J.; Sherry B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351. (j) Hashmi, A. S. K.; Rudolph, M. Chem. Soc. Rev. 2008, 37, 1766. (k) Michelet, V.; Toullec, P. Y.; Genêt, J. P. Angew. Chem., Int. Ed. 2008, 47, 4268. (l) Fürstner, A. Chem. Soc. Rev. 2009, 38, 3208.
    (13) For recent examples (a) Wolkenberg, S. E.; Wisnoski, D. D.; Leister, W. H.; Wang, Y.; Zhao, Z.; Lindsley, C. W. Org. Lett. 2004, 6, 1453. (b) Shipe, W. D.; Yang, F.; Zhao, Z.; Wolkenberg, S. E.; Nolt, M. B.; Lindsley, C. W. Heterocycles 2006, 70, 655. (c) Deng, X.; Mani, N. Org. Lett. 2006, 8, 269. (d) Held, I.; Xu, S. J.; Zipse, H. Synthesis 2007, 1185. (e) Rong, F.; Chow, S.; Yan, S.; Larson, G.; Hong, Z.; Wu, J. Bioorg. Med. Chem. Lett. 2007, 17, 1663. (f) Herrera, A. J.; Rond on, M.; Suarez, E. J. Org. Chem. 2008, 73, 3384. (g) Boyce, G. R.; Johnson, J. S. Angew. Chem., Int. Ed. 2010, 49, 8930.
    70
    (14) (a) Li, Z.; Ding, X.; He, C. J. Org. Chem. 2006, 71, 5876. (b) Li, Z.; Capretto, D. A.; Rahaman, R. O.; He, C. J. Am. Chem. Soc. 2007, 129, 12058. (c) Fantauzzi, S.; Caselli, A.; Gallo, E. Dalton Trans. 2009, 5434. (d) Diaz-Requejo, M. M.; Perez, P. J. Chem. Rev. 2008, 108, 3379. (e) Mueller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905.
    (15) Stephen C. Bergmeier, Tetrahedron 2000, 56, 2561.
    (16) (a) Sharpless, K. B.; Chong, A. O.; Oshima, J. J. Org. Chem. 1976, 41, 177. (b) Desai, L. V.; Sanford, M. S. Angew. Chem Int. Ed. 2007, 46, 5737. (c) Liu, G.; Stahl, S. J. Am. Chem. Soc. 2006, 128, 7179. (d) Michaelis, D. J.; Shaffer, C. J.; Yoon, T. P. J. Am. Chem. Soc. 2007, 129, 1866. (e) Williamson, K. S.; Yoon, T. J. Am. Chem. Soc. 2010, 132, 4570. (f) Alexanian, E. J.; Lee, C.; Sorenson, E. J. J. Am. Chem. Soc. 2005, 127, 7690. (g) Fache, F.; Schulz, E.; Tommasino, L. M.; Lemaire, M. Chem. Rev. 2000,100, 2159.(h) Davies, S. G.; Sanganee, H. J. Tetrahedron: Asymmetry 1995, 6, 671. (i) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480. (j) Legros, J.; Bolm, C. Angew. Chem., Int. Ed. 2004, 43, 4225.(k) Chen, Y. K.; Costa, A. M.; Walsh, P. J. J. Am. Chem. Soc. 2001, 123, 5378. (l) Vidal-Ferran, A.; Moyano, A.; Pericás, M. A.; Riera, A. J. Org. Chem. 1997, 62, 4970. (m) Vidal-Ferran, A.; Moyano, A.; Pericás, M. A.; Riera, A. Tetrahedron Lett. 1997, 38, 8773.(n) Reddy, K. S.; Solá , L.; Moyano, A.; Pericás, M. A.; Riera, A. J. Org. Chem. 1999, 64, 3969. (o) Reddy, K. S.; Solá , L.; Moyano, A.; Pericás, M. A.; Riera, A. Synthesis 2000, 2000, 165. (p) Jimeno, C.; Pasto, M.; Riera, A.; Pericás, M. A. J. Org. Chem. 2003, 68, 3130. (q) Pastá, M.; Riera, A.; Pericás, M. A. Eur. J. Org. Chem. 2002, 2337. (r) Garcıá-Delgado, N.; Fontes, M.; Pericás, M. A.; Riera, A.; Verdaguer, X. Tetrahedron: Asymmetry 2004, 15, 2085.
    (17) Laib, T.; Chastanet, J.; Zhu, J. J. Org. Chem. 1998, 63, 1709.
    (18) (a) Kang, S.-K.; Baik, T.-G.; Hur, Y. Tetrahedron 1999, 55, 6863. (b) Kimura, M.; Tanaka, S.; Tamaru, Y. J. Org. Chem. 1995, 60, 3764. (c) Knapp, S. Chem. Soc. Rev. 1999, 28, 61. (d) Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321.
    (19) (a) Li, G.; Chang, H.-T.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451. (b) Kramer, S.; Dooleweerdt, K.; Lindhardt, A. T.; Rottlfander, M.; Skrydstrup, T. Org. Lett. 2009, 11, 4208.
    (20) Sasai, H.; Tokunaga, T.; Watanabe, S.; Suzuki, T.; Itoh, N.; Shibasaki, M. J. Org. Chem. 1995, 60, 7388.
    (21) Bergmeier, S. C.; Stanchina, D. M. J. Org. Chem. 1999, 64, 2852.
    71
    (22) Ino, K.; Goto, S.; Nomura, S.; Isobe, K.-I.; Nawa, A.; Okamoto, T.; Tomoda, Y. Anticancer Res. 1995, 15, 2081.
    (23) (a) Stratmann, K.; Burgoyne, D. L.; Moore, R. E.; Patterson, G. M. L.; Smith, C. D. J. Org. Chem. 1994, 59, 7219. (b) Haddad, M.; Botuha, C.; Larcheveque, M. Synlett 1999, 1118.( c) O'Connell, C. E.; Salvato, K. A.; Meng, Z.; Littlefield, B. A.; Schwartz, C. E. Bioorg. Med. Chem. Lett. 1999, 9, 1541. (d) Wagner, B.; Gonzalez, G. I.; Dau, M. E. T. H.; Zhu, J. Bioorg. Med. Chem. 1999, 7, 737. (e) Dinh, T. Q.; Du, X.; Smith, C. D.; Armstrong, R. W. J. Org.Chem. 1997, 62, 6773.
    (24) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835.
    (25) (a) Cui, L.; Zhang, G.; Peng, Y.; Zhang, L. Org. Lett. 2009, 11, 1225. (b) Cui, L.; Peng, Y.; Zhang, L. J. Am. Chem. Soc. 2009, 131, 8394.(c) Mandal, S. K.; Roy, S. C. Tetrahedron 2007, 63, 11341. (d) Zinzalla, G.; Milroy, L.-G.; Ley, S. V. Org. Biomol. Chem. 2006, 4, 1977.
    (26) (a) Jadhav, A. M.; Bhunia, S.; Liao, H. Y.; Liu, R. S. J. Am. Chem. Soc. 2011, 133, 1769. (b) Benbow, J. F.; McClure, K. F.; Danishefsky, S. J. J. Am. Chem. Soc. 1993, 115, 12305. (c) McClure, K.; Benbow, J. F.; Danishefsky, S. J. J. Am. Chem. Soc. 1991, 113, 8185. (d) Yamamoto, Y.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 4128. (e) Wang, T.; Huang, X.-L.; Ye, S. Org. Biomol. Chem. 2010, 8, 5007.
    (27) (a) Yao, Q.; Zabawa, M.; Woo, J.; Zheng, C. J. Am. Chem. Soc. 2007, 129, 3088.( b) Zhang, Y.; Song, G.; Ma, G.; Zhao, J; Pan, C. L.; Li, X. Organometallics 2009, 28, 3233. (c)Yeom, H.-S.; Lee, J.-E.; Shin, S. Angew. Chem., Int. Ed. 2008, 47, 7040.
    (28) Murru, S.; Gallo, A. A.; Srivastava, R. S. ACS Catal. 2011, 1, 29.
    (29) (a) Yeom, H.-S; Lee, J.-E; Shin, S. Angew. Chem. Int. Ed. 2008, 47, 7040. (b) Mukherjee, A; Dateer, R.B.; Chaudhuri, R.; Bhunia, S.; Karad, S.N.; Liu, R.-S. J. Am. Chem. Soc. 2011, 133, 15372
    (1) For recent reviews on gold catalysis, see: (a) Krause, N.; Winter, C. Chem. Rev. 2011, 111,
    1994. (b) Aubert, C.; Fensterbank, L.; Garcia, P.; Malacria, M.; Simonneau, A. Chem. Rev. 2011,
    111, 1954. (c) Hashmi, A. S. K. Angew. Chem. Int. Ed. 2010, 49, 5232. d) Früstner, A. Chem.
    Soc. Rev.2009, 38, 3208. (e) Michelet, V.; Toullec, P. Y.; Genêt, J. P. Angew. Chem. Int. Ed.
    2008, 47, 4268. (f) Jiménez-Núñez, E.; Echavarren, A. M.; Chem. Rev. 2008, 108, 3326. (g) Li,
    Z.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239. (h) Arcadi, A. Chem. Rev. 2008, 108, 3266.
    (i) Gorin, D. J., Toste, F. D. Chem. Rev. 2008, 108, 3351. (j) Hashmi, A. S. K. Chem. Rev. 2007,
    107, 3180. (k) Fürstner, A.; Davies, P.W. Angew. Chem. Int. Ed. 2007, 46, 3410.
    (2) Bertz, S. H. J. Am. Chem. Soc. 1981, 103, 3599.
    (3) For general reviews on metal-catalyzed cycloadditions, see: (a) Lautens, M.; Klute M.; Tam,
    W. Chem. Rev., 1996, 96, 49. (b) Ojima, I.; Tzamarioudaki M.; Li, Z.; Donovan, R. J. Chem.
    Rev. 1996, 96, 635. (c) Fruhauf, H.-W. Chem. Rev., 1997, 97, 523.
    105
    (4) (a) Oshita, M.; Yamashita, K.; Tobisu M.; Chatani, N. J. Am. Chem. Soc., 2005, 127, 761. (b) Chatani, N.; Oshita, M.; Tobisu, M.; Ishii Y.; Murai, S. J. Am. Chem. Soc., 2003, 125, 7812. (c) Son S.; Fu, G. C. J. Am. Chem. Soc., 2007, 129, 1046.
    (5) Morimoto, T.; Chatani N.; Murai, S. J. Am. Chem. Soc., 1999, 121, 1758.
    (6) (a) Mandai, T.; Tsuji, J.; Tsujiguchi Y.; Saito, S. J. Am. Chem. Soc., 1993, 115, 5865. (b) Murakami, M.; Itami K.; Ito, Y. J. Am. Chem. Soc., 1997, 119, 2950. (c) Murakami, M.; Itami K.; Ito, Y. J. Am. Chem. Soc., 1999, 121, 4130. (d) Loebach, J. L.; Bennett D.M.; Danheiser, R. L. J. Am. Chem. Soc., 1998, 120, 9690.
    (7) (a) Eaton B. E.; Eollman, B.; J. Am. Chem. Soc., 1992, 114, 6245. (b) Sigman M. S.; Eaton, B. E. J. Am. Chem. Soc.1996, 118, 11783.
    (8) (a) Sigman, M. S.; Kerr C. E.; Eaton, B. E. J. Am. Chem. Soc. 1993, 115, 7545. (b) Sigman, M. S.; Eaton, B. E.; Heise J. D.; Kubiak, C. P. Organometallics, 1996, 15, 2829. (c) Sigman M. S.; Eaton, B. E. J. Org. Chem., 1994, 59, 7488.
    (9) (a) Storm, D. L.; Spencer, T. A. Tetrahedron Lett. 1967, 8, 1865. (b) Spencer, T. A.; Villarica, R. M.; Storm, D. L.; Weaver, T. D.; Friary,R. J.; Posler, J.; Shafer, P. R. J. Am. Chem. Soc. 1967, 89, 5497. (c) Murayama, S. T.; Spencer, T. A. Tetrahedron Lett. 1969, 10, 4479.
    (10) (a) Anac, O.; Daut, A. Liebigs Ann./Recl. 1997, 1249. (b) Anac, O.; Ozdemir, A. D.; Sezer, O. HelV. Chim. Acta 2003, 86, 290. (c) Anac, O.; Guengor, F. S.; Kahveci, C.; Cansever, M. S. HelV. Chim. Acta 2004, 87, 408. (d) Paulissen, R.; Hayez, E.; Hubert, A. J.; Teyssie, P. Tetrahedron Lett. 1974, 15, 607.
    (11) Liang, J.; Lo, M. M.-C.; Fu, G. C. Chem. Commun. 2000, 377.
    (12) For general reviews, see (a) Lautens, M.; Klute, W.; Tam, W. Chem. ReV. 1996, 96, 49. (b) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. ReV. 1996, 96, 635. (c) Frühauf, H.-W. Chem. ReV. 1997, 97, 523. (d) Schore, N. E. Chem.ReV. 1988, 88, 1081. Schore, N. E. Org. React. 1991, 40, 1. Geis, O.; Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1998, 37, 911. Schore, N. E. InComprehensiVe Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 1037. Schore, N. E. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier:New York, 1995; Vol. 12, p 703
    (13) For catalytic transformations of enynes using a transition-metal complexes as catalysts. (a) Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159. (b) Lee, B. Y.; Chung, Y. K.; Jeong, N.; Lee, Y.; Hwang, S. H. J. Am. Chem. Soc. 1994, 116, 8793. (c) Lee,
    106
    N. Y.; Chung, Y. K. Tetrahedron Lett. 1996, 37, 3145. Pagenkopf, B. L.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 2285. (d) Jeong, N.; Hwang, S. H.; Lee, Y. W.; Lim, J. S. J. Am. Chem. Soc. 1997, 119, 10549.(e) Kim, J. W.; Chung, Y. K. Synthesis 1998, 142. Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782. (f) Hicks, F. A.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 9450. (g) Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. (h) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. (i) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. (j) Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. (k) Jeong, N.; Lee, S.; Sung, B. K. Organometallics 1998, 17, 3642. (l) Morimoto, T.; Chatani, N.; Murai, S.; J. Am. Chem. Soc. 1999, 121, 1758.
    (14) Morcaccini, S.; Torroba, T. Org. Prep. Proced. Int. 1993, 25, 141. Moderhack, D. Synthesis 1985, 1083.
    (15) For recent papers on the use of GaCl3 as a catalyst, see: (a) Yonehara, F.; Kido, Y.; Morita, S.; Yamaguchi, M. J. Am. Chem. Soc. 2001, 123, 11310. (b) Kobayashi, K.; Arisawa, M.; Yamaguchi, M. J. Am. Chem. Soc. 2002, 124, 8528. (c) Chatani, N.; Inoue, H.; Kotsuma, T.; Murai, S. J. Am. Chem. Soc. 2002, 124, 10294.
    (16) Matsuo, J.; Odashima, K.; Kobayashi, S. Synlett 2000, 403.
    (17) W. He, C. Li.; L. Zhang, J. Am. Chem. Soc., 2011, 133, 8482.
    (18) (a) Ye, L.; Cui, L.; Zhang G.; Zhang, L. J. Am. Chem. Soc. 2010, 132, 3258. (b) Ye, L.; He W.; Zhang, L. J. Am. Chem. Soc., 2010, 132, 8550. (c) Ye, L.; He W.; Zhang, L. Angew. Chem., Int. Ed., 2011, 50, 3236. (d) He, W.; Li C.; Zhang, L. J. Am. Chem. Soc., 2011, 133, 8482.
    (19) For various tethered oxidants, see: (a) Li, G.; Zhang, L. Angew. Chem., Int. Ed. 2007, 46, 5156. (b) Shapiro, N. D.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 4160. (c) Yeom, H. S.; Lee, J. E.; Shin, S. Angew. Chem., Int. Ed. 2008, 47, 7040. (d) Cui, L.; Peng, Y.; Zhang, L. J. Am. Chem. Soc. 2009, 131, 8394. (e) Cui, L.; Zhang, G.; Peng, Y.; Zhang, L. Org. Lett. 2009, 11, 1225. (f) Yeom, H. S.; Lee, Y.; Lee, J. E.; Shin, S. Org. Biomol. Chem. 2009, 7, 4744. (g) Davies, P. W.; Albrecht, S. J. C. Angew. Chem., Int. Ed. 2009, 48, 8372. (h) Yeom, H. S.; Lee, Y.; Jeong, J.; So, E.; Hwang, S.; Lee, J. E.; Lee, S. S.; Shin, S. Angew. Chem., Int. Ed. 2010, 49, 1611. (i) Jadhav, A. M.; Bhunia, S.; Liao, H.-Y.; Liu, R.-S. J. Am. Chem. Soc. 2011, 133, 1769. (j) Yeom, H.- S.; So, E.; Shin, S. Chem.Eur. J. 2011, 17, 1764.
    107
    (20) For a recent intermolecular case using pyridine N-oxide, see: (a) Davies, P. W.; Cremonesi, A.; Martin, N. Chem. Commun. 2011, 47, 379. For an intermolecular gold-catalyzed nitrene transfer, see: Li, C.; Zhang, L. Org. Lett. 2011, 1738.
    (21) For synthesis of 2-aminofuran derivatives, see selected examples:(a) Oppenheimer, J.; Johnson, W. L.; Tracey, M. R.; Hsung, R. P.; Yao, P.-Y. ; Liu R.; Zhao, K.B. Org. Lett., 2007, 9, 2361.(b) Oh, C. H.; Reddy, V. T.; Kim A.; Rhim, C. Y.; Tetrahedron Lett., 2006, 47, 5307. (c) Steffen K.; Himbert, G. Chem. Ber.,1987, 120, 71. (d) Padwa, A.; Dimitroff, M.; Waterson A. G.; Wu, T. J. Org. Chem., 1997, 62, 4088. (e) Schlessinger R. H.; Bergstrom, C. P. Tetrahedron Lett., 1996, 37, 2133. (f) Freureand B. T.; Johnson, J. R. J. Am. Chem. Soc., 1931, 53, 1142.
    (22) Peng, X.-S.; Hou, X.-L. Prog. Heterocycl. Chem. 2011, 22, 181.
    (23) (a) Hashmi, A. S. K.; Häffner, T. H.; Rudolph, M.; Rominger, F. Eur. J. Org. Chem. 2011, 667 (b) Blanc, A.; Tenbrink, K.; Weibel, J.-M.; Pale, P. J. Org. Chem. 2009, 74, 4360 (c) Blanc, A.; Tenbrink, K.; Weibel, J.-M.; Pale, P. J. Org. Chem. 2009, 74, 5342. (d) Aponick, A.; Li, C.-Y. Malinge, J.; Marques, E. F. Org. Lett. 2009, 11, 4624. (e) Karpov, A. S.; Merkul, E.; Oeser, T.; Müller, T. J. J. Chem.Commun. 2005, 2581. (f) Jung, C.-K; Wang, J.-C.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4118. (g) Fürstner, A.; Gastner, T. Org. Lett. 2000, 2, 2467. (h) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem. Int. Ed. 2000, 39, 2285 (i) Trost, B. M.; McIntosh, M. C. J. Am. Chem. Soc. 1995, 117, 7255. (j) Katritzky, A. R.; Li, J.; J. Org. Chem. 1995, 60, 638. (k) Hashmi, A. S. K. Angew. Chem. Int. Ed. Engl. 1995, 34, 158. (l) Marshall, J. A.; Robinson, E. D. J. Org. Chem. 1990, 55, 3450.
    (24) (a) Davies, P. W.; Cremonesi A.; Martin, N. Chem. Commun., 2011, 47, 379. (b) Kramer, S.; Odabachian, Y.; Overgaard, J.; Rottander, M.; Gagosz F.; Skrydstrup, T. Angew. Chem., Int. Ed., 2011, 50, 5090. (c) Hashmi, A. S. K.; M. Bührle, Wölfle, Rudolph, M. M.; Wieteck, M.; Rominger F.; Frey, W. Chem. Eur. J., 2010, 16, 9846. (d) Cremonesi, A.; Dumitrescua L.; Davies, P. W. Angew. Chem., Int. Ed., 2011, 50, 8931.
    (25) (a) Davies, P. W.; Cremonesi, A.; Martin, N. Chem.Commun. 2011, 47, 379. (b) Li, C.; Zhang, L.; Org. Lett. 2011, 13, 1738. (c) Hashmi, A. S. K.; Rudolph, M.; Huck, J.; Frey, W.; Bats, J. W.; Hamzic, M. Angew. Chem. Int. Ed. 2009, 48, 5848. (d) Kramer, S.; Odabachian, Y.; Overgaard, J.; Rottlnder, M.; Gagosz, F.; Skrydstrup, T. Angew. Chem. Int. Ed. 2011, 50, 5090.
    (26) Selected examples; see (a) Ye, L.; Zhang, L. Org. Lett., 2009, 11, 3646. (b) Crone B.; Kirsch, S. F. J. Org. Chem. 2007, 72, 5435. (c) Buzas A.; Gagosz, F.Org. Lett., 2006, 8, 515. (d)
    108
    Buzas, A.; Istrate F.; Gagosz, F.Org. Lett., 2006, 8, 1957. (e) Liao H.-H.; Liu, R.-S.; Chem. Commun., 2011, 47, 1339.
    (27) (a) Kramer. S.; Skrydstrup, T. Angew. Chem. Int. Ed. 2012, 51, 4681. (b) Klumpp, D. A.; Zhang, Y.; O’Connor, M. J.; Esteves P. M.; de Almeida, L. S. Org. Lett. 2007, 9, 3085. (c) Dieker, J.; Frohlich R.; Wurthwien, E. U. Eu. J. Org. Chem. 2006, 5339.
    (28) Lee, C.B.; Chou, T.-C.; Zhang, X.-G.; Wang, Z.-G.; Kuduk, S.D.; Chappell, M.D.; Stachel, S.J.; Danishefsky, S.J. J. Org. Chem. 2000, 65, 6525.
    (1) (a) Trost, B. M. Acc. Chem. Res. 2002, 35, 695. (b) Trost, B. M. Angew. Chem. 1995, 107,
    285. Angew. Chem. Int. Ed. Engl. 1995, 34, 259. (c) Trost, B. M. Science. 1991, 254, 1471.
    (2) (a) Anastas, P.; Warner, J. C. in Green Chemistry, Theory and Practice, Oxford University
    Press, Oxford, 1998. (b) Anastas, P.T.; Kirchhoff, M. M. Acc. Chem. Res. 2002, 35, 686. (c)
    Anastas, P. T.; Zimmerman, J. B.; Environ. Sci. Technol. 2003, 37, 94A. (d) Poliakoff, M.;
    Fitzpatrick, J. M.; Farren, T. R.; Anastas, P. T. Science. 2002, 297, 807. (e) Trost, B. M.; Toste,
    D. F.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067.
    (3) (a) Janssen, E. M.W.; Folmer, J. C. W.; Wiegers, G. A. J. Less-Common Met. 1974, 38, 71.
    (b) Vogler, A.; Kunkely, H.; Coord. Chem. Rev. 2001, 219, 489. (c) Hashmi, A. S. K.; Blanco,
    M. C.; Fischer, D.; Bats, J. W. Eur. J. Org. Chem. 2006, 1387.
    (4) Tietze, L. F., Beifuss, U, Angew. Chem., Int. Ed. Engl. 1993, 32, 131.
    (5) For transition metal-catalyzed cycloaddition reactions, see: (a) Patil, N. T.; Yamamoto, Y.
    Chem. Rev. 2008, 108, 3395. (b) Lautens, M.; Klute, W.; Tam, W.Chem. Rev. 1996, 96, 49. (c)
    Fruhauf, H. W. Chem. Rev. 1997, 97, 523. (d) Winkler, J. D. Chem. Rev. 1996, 96, 167. (e)
    Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137. (f) Kagan, H. B.; Riant, O. Chem.
    Rev. 1992, 92, 1007. (g) Kusama, H.; Iwasawa, N. Chem Lett. 2006, 35, 1082. (h) Padwa, A.;
    Weingarten, M. D. Chem. Rev. 1996, 96, 223. (i) Mehta, G.; Muthusamy, S. Tetrahedron. 2002,
    139
    58, 9477. (j) McMills, M. C.; Wright, D. in Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, ed. by A. Padwa, W. H. Pearson, Wiley-Interscience, Hoboken, 2003, p. 253.
    (6) For recent reviews, see: (a) Royer, J.; Bonin, M.; Micouin, L. Chem. Rev. 2004, 104, 2285. (b) Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127. (c) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199. (d) McReynolds, M. D.; Dougherty, J. M.; Hanson, P. R. Chem. Rev. 2004, 104, 2239.
    (7) (a) Sasaki, T.; Yamakoshi, J.; Saito, M.; Kasai, K.; Matsudo, T. Biosci. Biotechnol. Biochem. 1998, 62, 1865. (b) Ottinger, H.; Soldo, T.; Hofmann, T. J. Agric. Food Chem. 2001, 49, 5383. (c) Vaittinen, S.-L.; Komulainen, H.; Kosma, V.-M.; Julkunene, A.; Maeki-Paakkanen, J. Food Chem. Toxicol. 1995, 33, 1027. (d) Moh, J. H.; Kim, J. K.; Jeong, Y. S.; Kim, J. Y.; Choi, Y. H.; Koh, H.-J. J. Med. Chem. 2004, 47, 792. (e) Vleet, T. R. V.; Klein, P. J.; Coulombe, R. A. J. Toxicol. Environ. Health 2002, 65, 853.
    (8) (a) Gottlieb, O. R. New Natural Products and Plant Drugs with Pharmacological, Biological, or Therapeutical ActiVity; Springer-Verlag: Berlin-Heidelberg, Germany, 1987; p 227. (b) Ward, R. S. Tetrahedron 1990, 46, 5029. (c) Fraga, B. M. Nat. Prod. Rep. 1992, 9, 217. (d) Merrit, A. T.; Ley, S. V. Nat. Prod. Rep. 1992, 9, 243. (e) Moody, C. J.; Davies, M. Stud. Nat. Prod. Chem. 1992, 10, 201. (f) Koert, U. Synthesis 1995, 115. (g) Benassi, R. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scrivan, E. F. V.; Bird, C. W.; Eds.; Elsevier: Oxford, U.K. 1996, Vol. 2, p 259. (h) Koch, S. S. C.; Chamberlin, A. R. Stud. Nat. Prod. Chem. 1995, 16, 687. (i) Ward, R. S. Nat. Prod. Rep. 1999, 16, 75.
    (9) For various methods of furan and dihydrofuran synthesis (a) Dean, F. M.; Sargent, M. V. In ComprehensiVe Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 4; pp 531-712. (b) Benassi, R. In ComprehensiVe Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996, Vol. 2, pp 259-436. (c) Fuentes, L. M.; Larson, G. L. Tetrahedron Lett. 1982, 23, 271. (d) Takano, S.; Iwabuchi, Y.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1989, 1371. (e) Pravia, K.; White, R.; Fodda, R.; Maynard, D. F. J. Org. Chem. 1996, 61, 6031. (f) Dalla, V.; Pale, P. Tetrahedron Lett. 1996, 37, 2781. (g) Alonso, I.; Carretero, J. C.; Garrido, J. L.; Magro, V.; Pedregal, C. J. Org. Chem. 1997, 62, 5682. (h) Garrido, J. L.; Alonso, I.; Carretero, J. C. J. Org. Chem. 1998, 63, 9406. (i) Ichikawa, J.; Fujiwara, M.; Wada, Y.; Okauchi, T.; Minami, T. Chem. Commun. 2000, 1887. (j)
    140
    Nguyen, V.-H.; Nishino, H.; Kurosawa, K. Tetrahedron Lett. 1996, 37, 4949. (k) Garzino, F.; Meon, A.; Brun, P. Tetrahedron Lett. 2000, 41, 9803. (l) Nair, V.; Mathew, J. J. Chem. Soc., Perkin Trans. 1 1995, 187. (m) Lee, Y. R.; Kim, B. S. Tetrahedron Lett. 1997, 38, 2095. (n) Davies, H. M. L.; Ahmed, G.; Calvo, R. L.; Churchill, M. R.; Churchill, D. G. J. Org. Chem. 1998, 63, 2641. (o) Lund, E. A.; Kennedy, I. A.; Fallis, A. G. Can. J. Chem. 1996, 74, 2401. (p) Schabbert, S.; Schauman, E. Eur. J. Org. Chem. 1998, 1873. (q) McDonald, F. E.; Connolly, C. B.; Gleason, M. M.; Towne, T. B.; Treiber, K. D. J. Org. Chem. 1993, 58, 6952. (r) Feldman, K. S.; Wrobleski, M. L. J. Org. Chem. 2000, 65, 8659.
    (10) Ma, S.; Zheng, Z.; Jiang, X. Org. Lett. 2007, 9, 526.
    (11) Buzas, A.; Istrate, F.; Gagosz, F. Org Lett. 2006, 9, 1957.
    (12) Trost, B. M.; Rhee. Y. H. J. Am. Chem. Soc. 2003, 125, 7482.
    (13) (a) Zeni, G.; Larock, R. C.Chem. Rev. 2004, 104, 2285. (b) Li, J. J.; Gribble, G. W. Palladium in Heterocyclic Chemistry; Pergamon: New York, 2000.
    (14) For Tungsten, see (a) Iwasawa, N.; Shido, M.; Kusama, H. J. Am. Chem. Soc. 2001, 123, 5814. (b) Kusama, H.; Funami, H.; Shido, M.; Hara, Y.; Takaya, J.; Iwasawa, N. J. Am. Chem. Soc. 2005, 127, 2709. (c) Iwasawa, N.; Shido, M.; Maeyama, K.; Kusama, H. J. Am. Chem. Soc. 2000, 122, 10226. (d) Kusama, H.; Shiozawa, F.; Shido, M.; Iwasawa, N. Chem. Lett. 2002, 124.
    (15) For Rhodium, (a) Shin, S.; Gupta, A. K.; Rhim, C. Y.; Oh, C. H. Chem. Commun. 2005, 4429. (b) Zhao, W.; Zhang, J. Org. Lett. 2011, 13, 688. (c) Lee, S. I.; Park, J. H.; Chung, Y. K.; Lee, S. G.; J. Am. Chem. Soc. 2004, 126, 2714. (d) Wender, P. A.; Paxton, T. J.; Williams, T. J. J. Am. Chem. Soc. 2006, 128, 14814. (e) Shibata, Y.; Noguchi, K.; Tanaka, K. J. Am. Chem. Soc. 2010, 132, 7896. (f) Konno, T.; Moriyasu, K.; Kinugawa, R.; Ishihara, T. Org. Biomol. Chem. 2010, 8, 1718.
    (16) For Gold, (a) Johansson, M. J.; Gorin, D. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 18002. (b) Carrillo, V. L.; Echavarren, A. M. J. Am. Chem. Soc. 2010, 132, 9292. (c) Melhado, A. D.; Luparia, M.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 12638. (d) Kim, N.; Kim, Y.; Park, W.; Sung, D.; Gupta, A. K.; Oh, C. H. Org. Lett. 2005, 7, 5289. (e) Li, C-W.; Lin, G-Y.; Liu, R-S. Chem. Eur. J. 2010, 16, 5803. (f) Zhang, G.; Zhang, L. J. Am. Chem. Soc. 2008, 130, 12598. (g) Shapiro, N. D.; Toste, F. D. J. Am. Chem. Soc. 2008, 130, 9244. (h) Gao, H.; Wu, X.; Zhang, J. Chem. Eur. J. 2011, 17, 2838. (i) Li, G.; Huang, X.; Zhang, L. J. Am. Chem. Soc. 2008, 130, 6944. (j) Asao, N.; Takahashi, K.; Lee, S.; Kasahara, T.; Yamamoto, Y. J. Am.
    141
    Chem. Soc. 2002, 124, 12650. (k) Asao, N.; Aikawa, H.; Yamamoto, Y.; J. Am. Chem. Soc. 2004, 126, 7458. (l) Asao, N.; Aikawa, H. J. Org. Chem. 2006, 71, 5249.
    (17) For Platinum, (a) Kusama, H.; Funami, H.; Takaya, J.; Iwasawa, N. Org. Lett, 2004, 6, 605. (b) Oh, C. H.; Lee, J. H.; Lee, S. J.; Kim, J. I.; Hong, C. S. Angew. Chem. Int. Ed. 2008, 47, 7505. (c) Zheng, H.; Zheng, J.; Yu, B.; Chen, Q.; Wang, X.; He, Y.; Yang, Z.; She, X. J. Am. Chem. Soc. 2010, 132, 1788. (d) Ishida, K.; Kusama, H.; Iwasawa, N. J. Am. Chem. Soc. 2010, 132, 8842. (e) Saito, K.; Sogou, H.; Suga, T.; Kusama, H.; Iwasawa, N. J. Am. Chem. Soc. 2011, 133, 689. (f) Kusama, H.; Miyashita, Y.; Takaya, J.; Iwasawa, N. Org. Lett, 2006, 8, 289. (g) Bhunia, S.; Wang, K-C.; Liu, R-S. Angew. Chem. Int. Ed. 2008, 47, 5063.
    (18) For Reviews on cycloaddition see, a) Lautens M.; Klute W.; Tam W. (b) Doyle, M. P. Chem. Rev. 1986, 86, 919.
    (19) For additional examples of intermolecular gold-catalyzed annulations, see: (a) Hsu, Y.-C.; Datta, S.; Ting, C.-M.; Liu, R.-S. Org. Lett. 2008, 10, 521. (b) Zhang, G.; Huang, X.; Li, G.; Zhang, L. J. Am. Chem. Soc. 2008, 130, 1814. (c) Barluenga, J.; Fernández-Rodríguez, M. A.; García- García, P.; Aguilar, E. J. Am. Chem. Soc. 2008, 130, 2764.
    (20) For selected examples on transition-metal-catalyzed [3+2] cycloaddition reactions, see: (a) Nakamura, I.; Yamamoto, Y.; Adv. Synth. Catal. 2002, 344, 111. (b) Viton, F.; Bernardinelli, G.; Kndig, E. P. J. Am. Chem. Soc. 2002, 124, 4968. (c) Trost, B. M.; Stambuli, J. P.; Silverman, S. M.; Schwcrer, U. J. Am. Chem. Soc. 2006, 128, 13328. d) Trost, B. M.; Silverman, S. M.; Stambuli, J. P. J. Am. Chem. Soc. 2007, 129,12398. (e) Kusama, H.; Ebisawa, M.; Funami, H.; Iwasawa, N. J. Am. Chem. Soc. 2009, 131, 16352. (f) Li, C.W.; Lin, G. Y.; Liu, R. S. Chem.
    Eur. J. 2010, 16, 5803. (g) Trost, B. M.; Silverman, S. M.; J. Am. Chem.Soc. 2010, 132, 8238.
    (21) Hongyin G.; Wu, X.; Zhang, J.; Chem. Eur. J. 2011, 17, 2838.
    (22) Liu, F.; Yu, Y.; Zhang, J. Angew. Chem. Int. Ed. 2009, 48, 5505.
    (23) For selected examples of 1, 2-acyloxy migration, see: (a) Correa, A.; Marion, N.; Fensterbank, L.; Malacria, M.; Nolan, S. P.; Cavallo, L. Angew. Chem., Int. Ed. 2008, 47, 718. (b) Ji, K.-G.; Shu, X.-Z.; Chen, J.; Zhao, S.-C.; Zheng, Z.-J.; Lu, L.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2008, 10, 3919. (c) Prasad, B. A. B.; Yoshimoto, F. K.; Sarpong, R. J. Am. Chem. Soc. 2005, 127, 12468. (d) Pujanauski, B. G.; Prasad, B. A. B.; Sarpong, R. J. Am. Chem. Soc. 2006, 128, 6786. (e) Motamed, M.; Bunnelle, E. M.; Singaram, S. W.; Sarpong, R. Org. Lett. 2007, 9, 2167. (f) Smith, C. R.; Bunnelle, E. M.; Rhodes, A. J.; Sarpong, R. Org. Lett. 2007, 6, 1169. (g)
    142
    Hardin, A. R.; Sarpong, R. Org. Lett. 2007, 9, 4547. (h) Soriano, E.; Marco-Contelles, J. J. Org. Chem. 2007, 72, 1443. (i) Mainetti, E.; Mouriès, V.; Fensterbank, L.; Malacria, M.; Marco-Contelles, J. Angew. Chem., Int. Ed. 2002, 41, 2132, and references therein.
    (24) Zheng, H.; Zheng, J.; Yu, B.; Chen, Q.; Wang, X.; He, Y.; Yang, Z.; She, X. J. Am. Chem. Soc. 2010, 132, 1788.
    (1) Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules; University Science Books: Sausalito, California 1999: Second Ed.
    (2) For general reviews, see: (a) Ho, T.-L. Topics of Organic synthesis; Wiley Interscience: New York, 1994: p. 79. (b) Tietze, L. F. Chem. Rev. 1996, 96, 115. (c) Winkler, J. D. Chem. Rev. 1996, 96, 167. (d) Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137.
    (3) (a) T. L. Ho. Tandem Organic Reactions, Wiley, New York, 1992. (b) Nicolaou, K. C.; Yue, E. W.; Oshima, T. in: N. Hall (Ed.), The New Chemistry, Cambridge University Press, Cambridge, 2001, p. 168. (c) Tietze, L. F.; Hautner, F.; Vögtle, J.F.; Stoddart, M. Shibasaki (Eds.), Stimulating Concepts in Chemistry, Wiley-VCH, Weinheim, 2000, p. 38; (d) Tietze, L. F.; Beifuss, U. Angew. Chem. 1993, 105. 137. Angew. Chem. Int. Ed. Engl. 1993. 32. 131.
    (4) O’Brien, P. Angew. Chem. Int. Ed. 1999, 38.
    (5) Li, G.; Sharpless, K. B. Angew. Chem. 1996, 108, 449; Angew. Chem. Int. Ed. Engl. 1996, 35, 451.
    (6) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
    (7) (a) Sharpless, K. B.; Patrick, D. W.; Truesdale, L. K.; Biller, S. A. J. Am. Chem. Soc. 1975, 97, 2305. (b) Sharpless, K. B.; Chong, A. O., Oshima, K. J. Org. Chem. 1976, 41, 177. (c) Herranz, E.; Biller, S. A.; Sharpless, K. B. J. Am. Chem.Soc. 1978, 100, 3596. (d) Herranz, E.; Sharpless, K. B. J. Org. Chem. 1979, 45, 2710.
    (8) Kolb, H. C.; Sharpless, K. B. Chem. Rev. 1944, 94, 2483.
    (9) Reviews for Sharpless aminohydroxylations of alkenes, see: (a) Nilov, D.; Reiser, O. Adv. Synth. Catal. 2002, 344, 1169. (b) O’Brien, P. Angew. Chem. Int. Ed. 1999, 38, 326. (c) Bodkin, J. A.; McLeod, M. D. J. Chem. Soc., Perkin Trans. 1, 2002, 2733
    (10) (a) Rudolph, J.; Sennhenn, P. C.; Vlaar, C. P.; Sharpless, K. B.; Angew. Chem. 1996, 108, 2991. (b). Li, G.; Angert, H. H.; Sharpless, K. B. Angew. Chem. 1996, 108, 2995. (c) Reddy, K. L.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 1207. (d) O‘Brien, P.; Osborne, S. A.; Parker, D. D. Tetrahedron Lett. 1998, 39, 4099. (e) O‘Brien, P.; Osborne, S. A.; Parker, D. D.; J. Chem. Soc. Perkin Trans. 1 1998, 2519. (f) Reddy, K. L.; Dress, K. R.; Sharpless, K. B. Tetrahedron
    174
    Lett. 1998, 39, 3667. (g) Bruncko, M.; Schlingloff, G.; Sharpless, K. B. Angew. Chem. 1997, 109, 1580.
    (11) (a) Hosokawa, T. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., Ed.; John Wiley & Sons: New York, 2002; Vol. 2, pp 2211-2225. (b) Tamaru, Y.; Kimura, M. Synlett 1997, 749. (c) Hegedus, L. S.; Allen, G. F.; Bozell, J. J.; Waterman, E. L. J. Am. Chem. Soc. 1978, 100, 5800.
    (12) (a) Dick, A. R.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 2300. (b) Desai, L. V.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 9542. (c) Dick, A. R.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 12790.
    (13) Alexanian, E. J.; Lee, C.; Sorensen, E. J. J. Am. Chem. Soc. 2005, 127, 7690.
    (14) Streuff, J.; Hovelmann, C. H.; Nieger, M.; Muniz, K. J. Am. Chem. Soc. 2005, 127, 14586.
    (15) Liu, G.; Stahl, S. J. Am. Chem. Soc. 2006, 128, 7179.
    (16) Desai, L. V.; Sanford, M. S. Angew. Chem. Int. Ed. 2007, 46, 5737.
    (17) Michaelis, D. J.; Shaffer, C. J.; Yoon, T. P. J. Am. Chem. Soc. 2007, 129, 1866.
    (18) Williamson, K. S.; Yoon, T. J. Am. Chem. Soc. 2010, 132, 4570.
    (19) For reviews on nitrone chemistry, see: a) Jones, R. C. F.; Martin J. N. in Synthetic Applications of 1, 3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, The Chemistry of Heterocyclic Compounds, Vol. 59 (Eds.: A. Padwa, W. H. Pearson), Wiley, New York, 2002, pp. 1 – 87; b) Rck-Braun, K.; Freysoldt, T. H. E.; Wierschem, F. Chem. Soc. Rev. 2005, 34, 507. c) Cardona, F.; Goti, A.; Angew. Chem. 2005, 117, 8042; Angew. Chem. Int. Ed. 2005, 44, 7832, and references therein.
    (20) Yeom, H.-S.; Lee, Y.; Jeong, J.; So, S.; Hwang, S.; Lee, E.-J.; Lee, S. S.; Shin.; S Angew. Chem. Int. Ed. 2010, 49, 1611
    (21) Mukherjee, A.; Dateer, R. B; Chaudhuri, R.; Bhunia, S.; Karad, S. N.; Liu, R.-S. J. Am. Chem. Soc. 2011, 133, 15372.
    (22) Lawrence, Cheung L. W.; Yudin, A.K. Org Lett. 6, 1281.

    無法下載圖示 全文公開日期 本全文未授權公開 (校內網路)
    全文公開日期 本全文未授權公開 (校外網路)

    QR CODE