新穎金屬催化有機反應運用在含氮與氧之雜環合成

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研究生：	帕加 vinayak vishnu pagar
論文名稱：	新穎金屬催化有機反應運用在含氮與氧之雜環合成 Development of New Organic Transformation for Synthesis of N, O-Containing Heterocycles by Using Metal Complexes
指導教授：	劉瑞雄
口試委員:	吳明忠陳銘洲蔡易州鄭建鴻劉瑞雄
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：	2014
畢業學年度：	102
語文別：	英文
論文頁數：	555
中文關鍵詞：	金金屬催化反應、氮氧雜環、波瓦羅夫反應
外文關鍵詞：	N, O-Containing Heterocycles, Oxa-Povarov Reaction
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簡介
本文介紹利用過渡金屬催化合成新型態的有機轉化合成反應。我們使用金及銠金屬使進行各種溫合和具有立體選擇性以及轉換效率高的反應，並且廣泛應用於合成氮和含雜環的化合物合成。為了提供方便和更好的解釋，本論文共分為四個章節。

　　第一章介紹nitrosobenzenes和alkenylgold金屬亞甲基之間的兩個新又優質的環加成反應。本章研究結果我們獲得更好的產率來自nitrosobenzenes和alkenyldiazo酯類之間的金催化的[3+3]環加成反應得到喹啉氧化物。例如炔丙基酯，其所得金亞甲基與nitrosobenzene反應，得到alkenylimine，隨後[4 +2]環加成反應用於nitrosobenzene以形成1, 2-oxazines。

　　第二章討論oxa-Povarov反應/亞甲基產生一系列的alkenyldiazocarbonyl化合物的發展。一個三氟甲磺酸催化乙烯基重氮基反應與二苯氧基甲基苯，得到含有重氮環加成並且具有立體選擇性成效卓越的化合物探討。在許多天然物以及生物活性分子出現以dihydrobenzopyran為核心的分子。

　　第三章的部分，探討vinyldiazo羰基物種和縮醛之間的金催化反應，得到選擇性E-configured alkyl 3,5-dimethoxy-5-pent-2- enoates並且有良好的產率。根據我們的實驗數據，該反應順序包括一個初始Prins型反應，隨後金–亞甲基生成。這類型反應的成功指出的重氮官能基上相鄰的碳陽離子穩定化的效果。

　　第四章使用金催化oxa-Povarov反應，其中包括合適的diaryloxymethylarenes和芳基取代烯烴反應得到dihydrobenzopyrans產物；他們的[4+2]環加成反應是由高效率金催化得到高立體選擇性催化。其環加成反應在溫合條件下均適用於廣泛的化合物。產物的分析闡釋了該反應可能經過一個逐步的離子反應機構，因為這兩個E-和Z位向的β-甲基苯乙烯，得到相同的環加成產物和相同的比例。

Abstract
This dissertation describes development of new synthetic organic transformations by using transition metal catalysis. The use of gold and rhodium metals enables mild, diastereoselective and efficient transformations of variety of readily available substrates to wide range of synthetically useful nitrogen and oxygen containing heterocyclic products. For convenience and better understanding, this thesis is divided into four chapters.
The first chapter describes the two new formal cycloaddition reactions between nitrosobenzenes and alkenylgold carbenoids. We obtained quinoline oxides in good to better yields from the gold-catalyzed [3+3]-cycloadditions between nitrosobenzenes and alkenyldiazo esters. For propargyl esters, its resulting gold carbenes react with nitrosobenzene to give alkenylimine, followed by a [4+2]-cycloaddition with nitrosobenzene to form 1, 2-oxazines.

The second chapter deals with the development of an oxa-Povarov reaction/carbene generation sequence for alkenyldiazocarbonyl compounds. A triflic acid catalyzed reaction of vinyl diazoacetate with diphenoxymethylbenzene to give diazo-containing cycloadducts stereoselectively with fruitful range of substrate scope. The dihydrobenzopyran core moiety found in many natural product and bioactive molecules.

The third chapter explains, the gold-catalyzed reactions between vinyldiazo carbonyl species and acetals to obtain selectively E-configured alkyl 3,5-dimethoxy-5-pent-2- enoates in good yields. According to our experimental data, this reaction sequence involves an initial Prins-type reaction, followed by gold-carbene generation. The success of this Prins-type reaction indicates a stabilization effect of the diazo functionality on the adjacent carbocation.

The fourth chapter provides gold-catalyzed oxa-Povarov reactions involving readily available diaryloxymethylarenes and aryl-substituted alkenes to give dihydrobenzopyrans; their [4+2]-cycloadditions are efficiently catalyzed by gold catalysis with high diastereoselectivity. The cycloadditions were applicable to broad range of substrate under ambient conditions. Product analysis reveals that the reaction likely proceeds via a stepwise ionic mechanism because both E- and Z-configured β-methylstyrene gave the same cycloadducts in the same proportions.

Contents

Acknowledgement                                                  VI   
Abstract                                             VIII
List of Schemes                                           X
List of Table                                         XIV
List of Figures                                                                                              XV
List of Publications                                      XVI 
Abbreviations                                          XVII



Chapter I: Gold-Catalyzed Formal [3 + 3] and [4 + 2] Cycloaddition Reactions of Nitrosobenzenes with Alkenylgold Carbenoids
    
        Introduction                                                                                                                 2
        Results and Discussion                                                                                              12
        Conclusion                                                                                                                 28
        Experimental Procedure                                                                                            28
        Reference                                                                                                                   32
        Spectroscopic Data                                                                                                    35
        X-ray crystallographic data                                                                                         57                                                
           1H  and  13C  NMR spectra                                                                                         67                 
        
Chapter II: Development of a Povarov Reaction/Carbene Generation Sequence for Alkenyldiazocarbonyl Compounds


        Introduction                                                                                                            174
        Results and Discussion                                                                                           181
        Conclusion                                                                                                              192
        Experimental Procedure                                                                                          193
        Reference                                                                                                                198
        Spectroscopic Data                                                                                                 201
        X-ray Crystallographic Data                                                                                     217                                                
           1H  and  13C  NMR Spectra                                                                                      230      


Chapter III: Gold-catalyzed Reactions between Alkenyldiazo Carbonyl Species and Acetals
         
         Introduction                                                                                                            304
         Results and Discussion                                                                                           312
         Conclusion                                                                                                              324
         Experimental Procedure                                                                                          325
         Reference                                                                                                                328
         Spectroscopic Data                                                                                                  332
         X-ray Crystallographic Data                                                                                     346                              
            1H and 13C NMR Spectra                                                                                        357      



Chapter IV: Gold-catalyzed Oxa-Povarov Reactions for the Synthesis of Highly Substituted Dihydrobenzopyrans from Diaryloxy- methylarenes and Olefins


         Introduction                                                                                                           427
         Results and Discussion                                                                                         435
         Conclusion                                                                                                            446
         Experimental Procedure                                                                                        446
         Reference                                                                                                               449
         Spectroscopic Data                                                                                                452
         X-ray Crystallographic Data                                                                                   467                                                
            1H and 13C NMR Spectra                                                                                     496      

                                

Chapter1
(1) (a) Kissane, M.; Maguire, A. R. Chem. Soc. Rev. 2010, 39, 845. (b) Martin, J. N.; Jones, R. C.; Padwa, A.; Pearson, W. H. John Wiley & Sons: Hoboken, NJ, 2003; Chapter 1. (c) Gothelf, K. V.; Kobayashi, S.; Jørgensen, K. A. Wiley-VCH: Weinheim, Germany, 2002; Chapter 6.
(2) (a) Zalatan, D. N.; Du, B. J. Top. Curr. Chem. 2010, 292, 347. (b) Lu, H.; Zhang, X. P. Chem. Soc. Rev. 2011, 40, 1899. (c) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147. (d) Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev. 2010, 110, 704.
(3) For selected reviews on gold catalysis, see the following: (a) Krause, N.; Winter, C. Chem. Rev. 2011, 111, 1994. (b) Corma, A.; LeyvaPerez, A.; Sabater, M. J. Chem. Rev. 2011, 111, 1657. (c) Yamamoto, Y.; Gridnev, I. D.; Patil, N. T.; Jin, T. Chem. Commun. 2009, 5075. (d) Abu Sohel, S. M.; Liu, R.-S. Chem. Soc. Rev. 2009, 38, 2269. (e) Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351. (f) Patil, N. T.; Yamamoto, Y. Chem. Rev. 2008, 108, 3395. (g) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180.
(4) (a) Doyle, M. P.; McKervy, M. A.; Ye, T. Modern Catalytic Method for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides; Wiley: New York, 1998. (b) Davies, H. M. L.; Beckwith, R. E. J. Chem. Rev. 2003, 103, 2861. (c) Shapiro, N. D.; Toste, F. D. Synlett 2010, 675.
(5) Doyle, M. P.; Yan, M.; Hu, W.; Gronenberg, L. J. Am. Chem. Soc. 2003, 125, 4692.
(6) Barluenga, J.; Lonzi, G.; Riesgo, L.; López, L. A.; Tomas, M. J. Am. Chem. Soc. 2010, 132, 13200.
(7) Reddy, R. P.; Davies, H. M. L. J. Am. Chem. Soc. 2007, 129, 10312.
(8) (a) Doyle, M. P.; Hu, W.; Timmons, D. J. Org. Lett. 2001, 3, 3741. (b) Shapiro, N. D.; Toste, F. D. J. Am. Chem. Soc. 2008, 130, 9244.
(9) Shapiro, N. D.; Shi, Y.; Toste, F. D. J. Am. Chem. Soc. 2009, 131, 11654.
(10) Wang, X.; Xu, X.; Zavalij, P.; Doyle, M. P. J. Am. Chem. Soc. 2011, 133, 16402.
(11) Selected examples: (a) Yamamoto, Y.; Yamamoto, H. Angew. Chem. Int. Ed. 2005, 44, 7082. (b) Nitsch, H; Kresze, G. Angew. Chem. Int. Ed. 1976, 15, 760. (c) Jana, C. K.; Studer, A. Angew. Chem. Int. Ed. 2007, 46, 6542. (d) Kumarn, S.; Shaw, D. M.; Longbottom, D. A.; Ley, S. V. Org. Lett. 2005, 7, 4189.
(12) (a) Penoni, A.; Palmisano, G.; Zhao, Y.-L.; Houk, K. N.; Volkman, J.; Nicholas, K. M. J. Am. Chem. Soc. 2009, 131, 653. (b) Murru, S.; Gallo, A. A.; Srivastava R. S. ACS Catal. 2011, 1, 29. (c) Penoni. A.; Nicholas, K. M. Chem. Commun. 2002, 484.
(13) Reviews for gold-catalyzed annulation or cycloaddition reactions, (a) Patil, N. T.; Yamamoto, Y. Chem. Rev. 2008, 108, 3395. (b) Fürstner, A.; Davies, P. W. Angew Chem. Int. Ed. 2007, 46, 3410.
(14) (a) Fürstner, A. Chem. Soc. Rev. 2009, 38, 3208. (b) Soriano, E.; Marco-Contelles. J. Acc. Chem.Res. 2009, 42, 1026 (c) Lee, S. I.; Chatani, N. Chem. Commun. 2009, 371. (d) Kirsch, S. F. Synthesis 2008, 3183 (e) Muzart. J. Tetrahedron, 2008, 64, 5815.
(15) (a) Hashmi, A. S. K. Angew.Chem. Int. Ed. 2008, 47, 6754. (b) Bongers, N.; Krause, N. Angew. Chem. Int. Ed. 2008, 47, 2178. (c) Hashmi, A. S. K. Angew.Chem. Int. Ed. 2005, 44, 6990. (d) Echavarren, A. M.; Nevado. C. Chem. Soc. Rev. 2004, 33, 431. (e) Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317.
(16) (a) Boorman, T. C.; Larrosa. I. Chem. Soc. Rev. 2011, 40, 1910. (b) Bandini. M., Chem. Soc. Rev. 2011, 40, 1358. (c) Krause, N.; Winter. C. Chem. Rev. 2011,111, 1994. (d) Rudolph, M.; Hashmi, A. S. K. Chem. Commun. 2011, 47, 6536. (e) Das, A.; Sohel, S. M. A.; Liu, R.-S. Org. Biomol. Chem. 2010, 8, 960.
(17) (a)Asao, N.; Takahashi, K.; Lee, S.; Kasahara, T.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 12650. (b) Gorin, D. J.; Toste, F. D. Nature. 2007, 446, 395. (c) Jiménez, N. E.; Echavarren, A. M. Chem. Rev. 2008, 108, 3326.
(18) 1,2-oxazines (a) Cesario, C.; Tardibono, L. P. Jr.; Miller, M. J. Tetrahedron Lett, 2010, 51, 3053. (b) Yan, S.; Miller, M. J.; Wencewicz, T. A.; Möllmann, U. Bioorg. Med. Chem. Lett. 2010, 20, 1302. (c) Cesario, C.; Miller, M. J. J. Org. Chem. 2009, 74, 5730. (d) Zhao, D.; Johansson, M.; Bäckvall, J.-E. Eur. J. Org. Chem. 2007, 26 4431.
(19) For examples of gold-catalyzed intermolecular cycloaddition reactions using propargyl esters, (a) Johansson, M. J.; Gorin, D. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 18002. (b) Gorin, D. J.; Watson, I. D. G.; Toste, F. D. J. Am. Chem. Soc. 2008, 130, 3736.
(20) Johansson, M. J.; Gorin, D. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 18002.
(21) Shapiro, N. D.; Toste, F. D. J. Am. Chem. Soc. 2008, 130, 9244.
(22) Yamamoto, Y.; Yamamoto, H. Angew. Chem. Int. Ed. 2005, 44, 7082.
(23) Doyle, M. P.; Hu, W.; Timmons, D. J. Org. Lett. 2001, 3, 3741.
(24) Shapiro, N. D.; Shi, Y.; Toste, F. D. J. Am. Chem. Soc. 2009, 131, 11654.
(25) Garayalde, D.; Krüger, K.; Nevado, C. Angew. Chem. Int. Ed. 2011, 50, 911.
(26) Xu, Z.-J.; Zhu, D.; Zeng, X.; Wang, F.; Tan, B.; Hou, Y.; Ly, Y.; Zhong, G. Chem. Commun. 2010, 46, 2504.
(27) Yamamoto, Y.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 4128.
(28) (a) Druellinger, M. L. J. Heterocycl. Chem. 1976, 13, 1001. (b) Xu, Z.-J.; Zhu, D.; Zeng, X.; Wang, F.; Tan, B.; Hou, Y.; Ly, Y.; Zhong, G. Chem. Commun. 2010, 46, 2504.
(29) X-ray crystallographic data of compound 1-3e is provided in Supporting Information.
(30) For the use of alkenylgold carbenoids to construct medium-sized carbocyclic rings, see (a) Gorin, D. J.; Watson, I. D. G.; Toste, F. D. J. Am. Chem. Soc. 2008, 130, 3736. (b) Garayalde, D.; Kruger. K.; Nevado, C. Angew. Chem. Int. Ed. 2011, 50, 911.
(31) Raczyńska, E. J.; Kosińska, W.; Osmialowski, B.; Gawinecki, R. Chem. Rev. 2005, 105, 3561.
(32) (a) Druellinger, M. L. J. Heterocycl. Chem. 1976, 13, 1001. (b) Xu, Z.-J.; Zhu, D.; Zeng, X.; Wang, F.; Tan, B.; Hou, Y.; Ly, Y.; Zhong, G. Chem. Commun. 2010, 46, 2504.
(33) This metathesis pathway is distinct from the nitroso/alkyne metathesis reported by us, see: Mukherjee, A.; Dateer, R. B.; Chaudhuri, R.; Bhunia, S.; Karad, S. N.; Liu, R.-S. J. Am. Chem. Soc. 2011, 133, 15372.

Chapter2
1. Selected reviews: (a) Doyle, M. P.; McKervy, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds, Wiley, New York, 1998 (b) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. (c) Davies, H. M. L.; Denton, J. R. Chem. Soc. Rev. 2009, 38, 3061. (d) Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev. 2010, 110, 704. (e) Davies, H. M. L.; Morton, D. Chem. Soc. Rev. 2011, 40, 1857. (f) Zhang, Z.; Wang, J. Tetrahedron 2008, 64, 6577.
2. (a) Babu, G.; Perumal, P. T. Aldrichimica Acta 2000, 33, 16. (b) Kouznetsov, V. V. Tetrahedron 2009, 65, 2721. (c) Sridharan, V.; Suryavanshi, P. A.; Menéndez, J. C. Chem. Rev. 2011, 111, 7157.
3. (a) Willis, N. J.; Bray, C. D.; Chem. Eur. J. 2012, 18, 9160. (b) Ferreira, S. B.; Silva da, F. C.; Pinto, A. C.; Gonzaga, D. T. G.; Ferreira, V. F. J. Heterocycl. Chem. 2009, 46, 1080. (c) Van de Water, R. W.; Pettus, T. R. R. Tetrahedron 2002, 58, 5367. (d) Korthals, K. A.; Wulff, W. D. J. Am. Chem. Soc. 2008, 130, 2898. (e) Inoue, T.; Inoue, S.; Sato, K. Bull. Chem. Soc. Jpn. 1990, 63, 1647.
4. Selected examples for carbocyclic cycloadducts see: (a) Deng, L.; Giessert, A. J.; Gerlitz, O. O.; Dai, X.; Diver, S. T.; Davies, H. M. L. J. Am. Chem. Soc. 2005, 127, 1342. (b) Davies, H. M. L. Adv. Cycloaddit. 1999, 5, 119. (c) Davies, H. M. L.; Xing, B.; Kong, N.; Stafford, D. G. J. Am. Chem. Soc. 2001, 123, 7461. (d) Davies, H. M. L.; Clark, T. J.; Smith, H. D. J. Org. Chem. 1991, 56, 3819. (e) Liu, Y.; Bakshi, K.; Zavalij, P.; Doyle, M. P. Org. Lett. 2010, 12, 4304.
5. For oxacyclic cycloadducts, see: (a) Xu, X.; Hu, W.-H.; Zavalij, P.; Doyle, M. P. Angew. Chem. Int. Ed. 2011, 50, 11152. (b) Doyle, M. P.; Hu, W.; Timmons, D. J. Org. Lett. 2001, 3, 3741. (c) Zhou, L.; Doyle, M. P. J. Org. Chem. 2009, 74, 9222.
6. For azacyclic cycloadducts, see selected papers: (a) Doyle, M. P.; Yan, M.; Hu, W.; Gronenberg, L. J. Am. Chem. Soc. 2003, 125, 4692. (b) Barluenga, J.; Lonzi, G.; Riesgo, L.; Lpez, L. A.; Tomas, M. J. Am. Chem. Soc. 2010, 132, 13200. (c) Yan, M. Jacobsen, N.; Hu, W.; Gronenberg, L. S.; Doyle, M. P.; Colyer, J. T.; Bykowski, D. Angew. Chem. Int. Ed. 2004, 43, 6713. (d) Wang, X.; Xu, X.; Zavalij, P.; Doyle, M. P. J. Am. Chem. Soc. 2011, 133, 16402.
7. For alkaloid synthesis using Povarov approach, see: (a) Grieco, P. A.; Kaufman, M. D. J. Org. Chem. 1999, 64, 7586. (b) Powell, D. A.; Batey, R. A. Org. Lett. 2002, 4, 2913. (c) Kende, A. S.; Fan, J.; Chen, Z. Org. Lett. 2003, 5, 3205. (d) Twin, H.; Batey, R. A. Org. Lett. 2004, 6, 4913. (e) Huang, Y.; Zhang, J.; Pettus, R. R. Org. Lett. 2005, 7, 5841. (f) Tapas, A. R.; Sakarkar, D. M.; Kakde, R. B. Top. J. Pharm. Res. 2008, 7, 1089.
8. (a) Batey, R. A.; Powell, D. A. Chem. Commun. 2001, 2362. (b) Strekowski, L.; Say, M.; Henary, M.; Ruiz, P.; Manzel, L.; Macfarlane, D. E.; Bojarski, A. J. J. Med. Chem. 2003, 46, 1242. (c) Michael, J. P. Nat. Prod. Rep. 2004, 21, 650. (d) Michael, J. P. Nat. Prod. Rep. 2007, 24, 223. (e) Mar, W.; Lee, H. T.; Je, K. H.; Choi, H. Y.; Seo, E. K.; Arch. Pharm. Res. 2003, 26,147. (f) Jacobsen, E. J.; VanDoornik, F. J.; Ayer, D. E.; Belonga, K. L.; Braughler, J. M.; Hall, E. D.; Houser, D. J. J. Med. Chem. 1992, 35, 4464. (g) Cassidy, F.; Evans, J. M.; Hadley, M. S.; Haladij, A. H.; Leach, P. E.; Stemp, G. J. Med. Chem. 1992, 35, 1623.
9. Gharpure, S. J.; Sathiyanarayanan, A. M.; Vuram, P. K. RSC Advance 2013, 3, 18279.
10. Povarov reactions refer to the formal [4+2] cycloadditions of N-aryl imines with enol ethers or enamines. See reviews: (a) Povarov, L. S. Russ. Chem. Rev. 1967, 36, 656. (b) Kouznetsov, V. V.; Tetrahedron. 2009, 65, 2721. (c) Bello, D.; Ramon, R.; Lavilla, R. Curr. Org. Chem. 2010, 14, 332.
11. For Povarov reactions catalyzed by Brønsted acids, see selected examples: (a) Xu, H.; Zuend, S. J.; Woll, M. G.; Tao, Y.; Jacobson, E. N. Science 2010, 327, 986. (b) Akiyama, T.; Morita, H.; Fuchibe, K. J. Am. Chem. Soc. 2006, 128, 13070. (c) Liu, H.; Dagousset, G.; Masson, G.; Retailleau, P.; Zhu, J. J. Am. Chem. Soc. 2009, 131, 4598. (d) Dagousset, G.; Zhu, J. G. Masson, J. Am. Chem. Soc. 2011, 133, 14804.
12. Tanimoto, S.; Iwata, S.; Imanishi, T.; Okano, M. Bull. Int. Chem. Res., Kyoto Uni. 1978,
56, 101.
13. For the preferable E-alkene selectivity of gold carbenes, see selected examples: (a) Lu, B.; Li, C.; Zhang, L. J. Am. Chem. Soc. 2010, 132, 14070. (b) Li, G.; Zhang, G.; Zhang, L. J. Am. Chem. Soc. 2008, 130, 3740. (c) Wang, S.; Zhang, L. Org. Lett. 2006, 8, 4585. (d) Davies, P. W.; Cremonesi, A.; Martin, N. Chem. Commun. 2011, 47, 379.
14. The crystallographic data of compounds 2-16a was provided in Supporting Information.
15. For the Z-alkene selectivity of rhodium carbenes; see selected examples: (a) Taber, D. F.; Sheth, R. B.; Joshi, P. V.; J. Org. Chem. 2004, 69, 4276. (b) Davies, H. M. L.; Hedley, S. J. Chem. Soc. Rev. 2007, 36, 1109. (c) Ota, K.; Chatani, N.; Chem. Commun. 2008, 2906. (d) Lian, Y.; Davies, H. M. L. Org. Lett. 2010, 12, 924.
16. (a) Adam, W.; Bialas, J.; Hadjiarapoglou, L. P. Chem. Ber. 1991, 124, 2377. (b) Trost, B. M.; Malhotra, S.; Koschker, P.; Ellerbrock, P. J. Am. Chem. Soc. 2012, 134, 2075.
17. Taylor, R. R. R.; Batey, R. A. J. Org. Chem. 2013, 78, 1404.

Chapter3
(1) (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (b) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813. (c) Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067. (d) Fruhauf, H. W. Chem. Rev. 1997, 97, 523.
(2) For selected examples, see: (a) Brummond, K. M.; Lu, J. J. Am. Chem. Soc. 1999, 121, 5087. (b) Kablaouni, N. M.; Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 5818. (c) Chatani, N.; Morimoto, T,; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1996, 120, 5335. (d) Shibata, T.; Toshida, N.; Takagi, K. Org. Lett. 2002, 4, 1619.
(3) (a) Doyle, M. P.; Yan, M.; Hu, W.; Gronenberg, L. J. Am. Chem. Soc. 2003, 125, 4692. (b) Barluenga, J.; Lonzi, G.; Riesgo, L.; López, L. A.; Tomas, M. J. Am. Chem. Soc. 2010, 132, 13200. (c) Reddy, R. P.; Davies, H. M. L. J. Am. Chem. Soc. 2007, 129, 10312. (d) Doyle, M. P.; Hu, W.; Timmons, D. J. Org. Lett. 2001, 3, 3741. (e) Shapiro, N. D.; Toste, F. D. J. Am. Chem. Soc. 2008, 130, 9244. (f) Shapiro, N. D.; Shi, Y.; Toste, F. D. J. Am. Chem. Soc. 2009, 131, 11654. (g) Wang, X.; Xu, X.; Zavalij, P.; Doyle, M. P. J. Am. Chem. Soc. 2011, 133, 16402.
(4) Selected reviews: (a) Davies, H. M. L.; Morton, D. Chem. Soc. Rev. 2011, 40, 1857. (b) Doyle, M. P.; Duﬀy, R.; Ratnikov, M.; Zhou, L. Chem. Rev. 2010, 110, 704. (c) Manning, J. R.; Davies, H. M. L. Nature, 2008, 451, 417. (d) Doyle, M. P.; McKervy, M. A.; Ye, T. Modern Catalytic Method for Organic Synthesis with Diazo Compounds; John Wiley & Sons: Wiley; New York, 1998. (e) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. (f) Davies, H. M. L.; Denton, J. R. Chem. Soc. Rev. 2009, 38, 3061. (g) Zhang, Z.; Wang, J. Tetrahedron, 2008, 64, 6577.
(5) Selected examples for carbocyclic cycloadducts, see: (a) Briones, J. F.; Davies, H. M. L. J. Am. Chem. Soc. 2013, 135, 13314. (b) Liu, Y.; Bakshi, K.; Zavalij, P.; Doyle, M. P. Org. Lett. 2010, 12, 4304. (c) Davies, H. M. L. Adv. Cycloaddition 1999, 5, 119. (d) Davies, H. M. L.; Xing, B.; Kong, N.; Stafford, D. G. J. Am. Chem. Soc. 2001, 123, 7461. (e) Davies, H. M. L.; Clark, T. J.; Smith, H. D. J. Org. Chem. 1991, 56, 3819. (f) Olson, J. P.; Davies, H. M. L. Org. Lett. 2008, 10, 573. (g) Deng, L.; Giessert, A. J.; Gerlitz, O. O.; Dai, X.; Diver, S. T.; Davies, H. M. L. J. Am. Chem. Soc. 2005, 127, 1342.
(6) For oxacyclic cycloadducts, see: (a) Xu, X.; Hu, W.-H.; Zavalij, P. Y.; Doyle, M. P. Angew. Chem. Int. Ed. 2011, 50, 11152. (b) Davies, H. M. L.; Ahmed, G.; Churchill, M. R. J. Am. Chem. Soc. 1996, 118, 16774. (c) Doyle, M. P.; Hu, W.; Timmons, D. J. Org. Lett. 2001, 3, 3741.
(7) For azacyclic cycloadducts, see (a) Doyle, M. P.; Yan, M.; Hu, W.; Gronenberg, L. J. Am. Chem. Soc. 2003, 125, 4692. (b) Padwa, A.; Kulkarni, Y. S.; Zhang, Z. J. J. Org. Chem. 1990, 55, 4144. (c) Barluenga, J.; Lonzi, G.; Riesgo, L.; López, L. A.; Tomas, M. J. Am. Chem. Soc. 2010, 132, 13200. (c) Yang, M.; Jacobsen, N.; Hu, W.; Gronenberg, L. S.; Doyle, M. P.; Colyer, J. T.; Bykowski, D. Angew. Chem. Int. Ed. 2004, 43, 6713. (d) Wang, X.; Xu, X.; Zavalij, P.; Doyle, M. P. J. Am. Chem. Soc. 2011, 133, 16402. (e) Lian, Y.; Davies, H. M. L. J. Am. Chem. Soc. 2010, 132, 440. (f) Xu, X.; Ratnikov, M. O.; Zavalij, P. Y.; Doyle, M. P. Org. Lett. 2011, 13, 6122.
(8) (a) Liu, Y.; Zhang, Y.; Jee, N.; Doyle, M. P. Org. Lett. 2008, 10, 1605. (b) Doyle, M. P.; Kundu, K.; Russel, A. E. Org. Lett. 2005, 7, 5171. (c) Deng, G.; Tian, X.; Qu, Z.; Wang, J. Angew. Chem. Int. Ed. 2002, 41, 2773. (d) Calter, M. A.; Sugathapala, P. M.; Zhu, C. Tetrahedron Lett. 1997, 38, 3837.
(9) Jadhav, A. M.; Pagar, V. V.; Liu, R.-S. Angew. Chem. Int. Ed. 2012, 51, 11809.
(10) Reviews for the Povarov reactions, see: (a) Povarov, L. S. Russ. Chem. Rev. 1967, 36, 656. (b) Kouznetsov, V. V. Tetrahedron 2009, 65, 2721,(c) Bello, D.; Ramón, R.; Lavilla, R. Curr. Org. Chem, 2010, 14, 332. (d) McCarrick, M. A.; Wu, Y. D.; Houk, K. N. J. Org. Chem. 1993, 58, 3330.
(11) The crystallographic data of unsaturated acid 3-7a’ was provided in Supporting Information.
(12) For reviews on the Prins cyclization, see (a) Adams, D. R.; Bhatnagar, S. P. Synthesis, 1977, 661. (b) Snider, B. B. in The Prins Reactions and Carbonyl-ene Reactions; Trost, B. M.; Fleming, I.; Heathcock, C. H.; Eds. Pergamon Press: New York, 1991, Vol. 2, pp 527. (c) Overman, L. E.; Pennington, L. D. J. Org. Chem. 2003, 68, 7143.
(13) For selected examples, see: (a) Jasti, R.; Rychnovsky, S. D. J. Am. Chem. Soc. 2006, 128, 13640. (b) Lee, C.-H. A.; Loh, T.-P. Tetrahedron Lett. 2006, 47, 1641. (c) Overman, L. E.; Veltthuisen, E. J. J. Org. Chem. 2006, 71, 1581. (d) Bolla, M. L.; Patterson, B.; Rychnovsky S. D. J. Am. Chem. Soc 2005, 127, 16044. (e) Barry, C. S. J.; Crosby, S. R.; Harding, J. R.; Hughes, R. A.; King, C. D.; Parker, G. D.; Willis, C. L. Org. Lett. 2003, 5, 2429. (f) Miranda, P. O.; Diaz, D. D.; Padron, J. I.; Bermejo, J.; Martin, V. S. Org. Lett 2003, 5, 1979.
(14) For the preferable E-alkene selectivity of gold carbenes, see ref. 8 and selected examples: (a) Lu, B.; Li, C.; Zhang, L. J. Am. Chem. Soc. 2010, 132, 14070. (b) Li, G.; Zhang, G. Zhang, L. J. Am. Chem. Soc. 2008, 130, 3740. (c) Wang, S.; Zhang, L. Org. Lett. 2006, 8, 4585. (d) Davies, P. W.; Cremonesi, A.; Martin, N. Chem. Commun. 2011, 47, 379.
(15) For the Z-alkene selectivity of rhodium carbenes; see selected examples: (a) Taber, D. F.; Joshi, P. V. J. Org. Chem. 2004, 69, 4276. (b) Davies, H. M. L.; Hedley, S. J. Chem. Soc. Rev. 2007, 36, 1109. (c) Ota, K.; Chatani, N. Chem. Commun. 2008, 2906. (d) Lian, Y.; Davies, H. M. L. Org. Lett. 2009, 12, 924. (e) Lian, Y.; Davies, H. M. L. Org. Lett. 2012, 14, 1934.

Chapter4
(a) Babu, G.; Perumal, P. T. Aldrichimica Acta 2000, 33, 16. (b) Kouznetsov, V. V. Tetrahedron 2009, 65, 2721. (c) Sridharan, V.; Suryavanshi, P. A.; Menéndez, J. C. Chem. Rev. 2011, 111, 7157.
(2) Povarov reactions refer to the formal [4+2]-cycloadditions of N-aryl imines with enol ethers or enamines. See reviews: a) Povarov, L. S. Russ. Chem. Rev. 1967, 36, 656. (b) Bello, D.; Ramón, R.; Lavilla, R. Curr. Org. Chem, 2010, 14, 332. (c) McCarrick, M. A.; Wu, Y. D.; Houk, K. N. J. Org. Chem. 1993, 58, 3330. (d) Whiting, A.; Windsor, C. M. Tetrahedron 1998, 54, 6035.
(3) Povarov reactions catalyzed by Brønsted acids, see selected examples: (a) Xu, H.; Zuend, S. J.; Woll, M. G.; Tao, Y.; Jacobson, E. N. Science 2010, 327, 987. (b) Akiyama, T.; Morita, H.; Fuchibe, K. J. Am. Chem. Soc. 2006, 128, 13070. (c) Liu, H.; Dagousset, G.; Masson, G.; Retailleau, P.; Zhu, J. J. Am. Chem. Soc. 2009, 131, 4598. (d) Dagousset, G.; Zhu, J.; Masson, G. J. Am. Chem. Soc. 2011, 133, 14804. (e) Ishitani, H.; Kobayashi, S. Tetrahedron Lett. 1996, 37, 7375. (f) Bergonzini, G.; Gramigna, L.; Mazzanti, A.; Fochi, M.; Bernardi, L.; Ricci, A. Chem. Commun. 2010, 46, 327. (g) He, L.; Bekkaye, M.; Retailleau, P.; Masson, G. Org. Lett. 2012, 14, 3158.
(4) Xia, Y.; Yang, Z.-Y.; Xia, P.; Bastow, K. F.; Tachibana, Y.; Kuo, S.-C.; Hamel, E.; Hackl, T.; Lee, K.-H.; J. Med. Chem. 1998, 41, 1155. (b) Damon, D. B.; Dugger, R. W.; Scott, R.W.; U.S. Patent 6, 689, 897, 2004. (c) Powell, D. A.; Batey, R. A. Org. Lett. 2002, 4, 2913. (d) Matsuhisa, A.; Kikuchi, K.; Sakamoto, K.; Yatsu, T.; Tanaka, A. Chem. Pharm. Bull. 1999, 47, 329. (e) Li, C.; Li, X.; Hong, R. Org. Lett. 2009, 11, 4036.
(5) (a) Wang, J.; Xu, F.- X.; Lin, X.-F.; Wang, Y.-G. Tetrahedron Lett. 2008, 49, 5208. (b) Wang, X.-S.; Li, Q.; Yao, C.-S.; Tu, S.-J. Eur. J. Org. Chem. 2008, 3513. (c) Wang, X.-S.; Li, Q.; Wu, J.-R.; Tu, S.-J. J. Comb. Chem. 2009, 11, 433. (d) Jin, G.; Zhao, J.; Han, J.; Zhu, S.; Zhang, J. Tetrahedron 2010, 66, 913.
(6) (a) Meng, X.; Huang, Y.; Zhao, H.; Xie, P.; Ma, J.; Chen, R. Org. Lett. 2009, 11, 991. (b) Korthals, K. A.; Wulff, W. D. J. Am. Chem. Soc. 2008, 130, 2898. (c) Ko, S. K.; Jang, H. J.; Kim, E.; Park, S. B. Chem. Commun. 2006, 2962. (d) Van de Water, R. W.; Pettus, T. R. R. Tetrahedron 2002, 58, 5367. (e) Kotame, P.; Hong, B.-C.; Liao, J. H. Tetrahedron Lett. 2009, 50, 704. (f) Mente, N. R.; Neighbors, J. D.; Wiemer, D. F. J. Org. Chem. 2008, 73, 7963.
(7) (a) Huang, Y.; Zhang, J.; Pettus, T. R. R. Org. Lett. 2005, 7, 5841. (b) Tapas, A. R.; Sakarkar, D. M.; Kakde, R. B. Top. J. Pharm. Res. 2008, 7, 1089.
(8) (a) Tolman, R. L.; Chin, A. C. Telomerase inhibitors and methods of their use. W.O. Patent 0,193,864, Dec 13, 2001. (b) Mar, W.; Lee, H.T.; Je, K.H.; Choi, H. Y.; Seo, E. K. Arch. Pharm. Res. 2003, 26,147. (c) Jacobsen, E. J.; VanDoornik, F. J.; Ayer, D. E.; Belonga, K. L.; Braughler, J. M.; Hall, E. D.; Houser, D. J. J. Med. Chem. 1992, 35, 4464. (d) Cassidy, F. J.; Evans, M.; Hadley, M. S.; Haladij, A. H.; Leach, P. E.; Stemp, G. J. Med. Chem. 1992, 35, 1623. (e) Pouget, C.; Fagnere, C.; Basly, J.-P.; Leveque, H.; Chulia, A.-J. Tetrahedron 2000, 56, 6047.
(9) (a) Gharpure, S. J.; Sathiyanarayanan, A. M.; Vuram, P. K. RSC Advance 2013, 3, 18279. (b) Willis, N. J.; Bray, C. D. Chem. Eur. J. 2012, 18, 9160. (c) Ferreira, S. B.; da Silva, F. de C.; Pinto, A. C.; Gonzaga, D. T. G.; Ferreira, V. F. J. Heterocycl. Chem. 2009, 46, 1080. (d) Van de Water, R. W.; Pettus, T. R. R. Tetrahedron 2002, 58, 5367. (e) Korthals, K. A.; Wulff, W. D. J. Am. Chem. Soc. 2008, 130, 2898 (f) Inoue, T.; Inoue, S.; Sato, K. Bull. Chem. Soc. Jpn. 1990, 63, 1647.
(10) Maity, P.; Srinivas, H. D.; Watson, M. P. J. Am. Chem. Soc. 2011, 133, 17142.
(11) Taylor, R. R.; Batey, R. A. J. Org. Chem. 2013, 78, 1404.
(12) Jadhav, A. M.; Pagar, V. V.; R.-S. Liu, Angew. Chem. Int. Ed. 2012, 51, 11809.
(13) Nakatani, K.; Higashida, N.; Saito, I. Tetrahedron Lett. 1997, 38, 5005.
(14) The crystallographic data of compounds 4-3a and 4-3g were provided in Supporting Information; these data were also deposited in Cambridge crystallographic center (4-3a CCDC 996266; 4-3g CCDC 996267).
(15) Tanimoto, S.; Iwata, S.; Imanishi, T.; Okano, M. Bull. Int. Chem. Res., Kyoto Uni. 1978, 56, 101.
(16) (a) Tietze, L. F.; Kinzel, T.; Schmatz, S. J. Am. Chem. Soc. 2006, 128, 11483. (b) Carlier, P. R.; Lo, K. M.; Lo, M. M-C.; Williams, I. D. J. Org. Chem. 1995, 60, 7511. (c) Tomoda, S. Chem. Rev. 1999, 99, 1243. (d) Green, A. J.; Kuan, Y.-L.; White, J. M. J. Org. Chem. 1995, 60, 2734.
(17) For reviews on gold-catalyzed cycloaddition reactions, see: (a) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180. (b) Furstner, A. Chem. Soc. Rev. 2009, 38, 3208. (c) Patil, N. T.; Yamamoto, Y. Chem. Rev. 2008, 108, 3395. (d) Abu Sohel, S. M.; Liu, R.-S. Chem. Soc. Rev. 2009, 38, 2269. (e) Lopez, F.; Mascarenas, J. L. Beilstein J. Org. Chem. 2011, 76, 1075. (f) Aubert, C.; Fensterbank, L.; Garcia, P.; Malacria, M.; Simonneau, A. Chem. Rev. 2011, 111, 1954. (g) Qian, D.; Zhang, J. Chem. Rec. 2014, 14, 280.
(18) Selected papers: (a) Karad, S. N.; Bhunia, S.; Liu, R.-S. Angew. Chem. Int. Ed. 2012, 51, 8726. (b) Chen, C. -H.; Tsai, Y. -C.; Liu, R.-S. Angew. Chem. Int. Ed. 2013, 52, 4599. (c) Johnson, M. W.; Bagley, S. W.; Mankad, N. P.; Bergman, R. G.; Mascitti, V.; Toste, F. D. Angew. Chem. Int. Ed. 2014, 53, 4404. (d) Bucher, J.; Wurm, T.; Nalivela, K. S.; Rominger, R. F.; Hashmi, A. S. K. Angew. Chem. Int. Ed. 2014, 53, 3854. (e) Wang, Y.; Yepremyan, A.; Ghorai, S.; Todd, R.; Aue, D. H.; Zhang, L. Angew. Chem. Int. Ed. 2013, 52, 7795. (f) Obradors, C.; Echavarren, A. M, Chem. Eur. J. 2013, 19. 3547.

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