第一部分是利用(+)-Ketopinic Acid 衍生之□-胺基醇為掌性配位基進行炔基對醛類的不對稱加成反應；第二部分是利用Sulfonamide 作為掌性配位基進行二乙基鋅對共軛烯酮的不對稱加成反應。

The application of camphor derived chiral ligands in catalytic asymmetric catalysis are described in this thesis which consists of two parts. The first part describes the asymmetric addition of zinc acetylide to aldehyde catalyzed by chiral □-amino alcohol 16, derived from (+)-ketopinic acid. The second part describes the asymmetric addition of Et2Zn to conjugated enone catalyzed by sulfonamide.

參 考 文 獻

1.(a) Stinson, S.C. Chem. Eng. News 1993, 71, 28. (b) Stinson, S. C. Chem. Eng. News 1994, 72, 38. (c) Stinson, S. C. Chem. Eng. News 1995, 73, 44. (d) Stinson, S. C. Chem. Eng. News 1997, 75, 38.
2.Seyden-penne J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis , John-Wiley and sons, New York, 1995.
3.Calne, D. B.; Sandlar, M. Nature 1970, 226, 21.
4."Reagents, Catalysts and Building Blocks for Enantioselective Synthesis Resolving Agent" Merck's Chiralica.
5.Stinson, S. C. Chem. Eng. News 1992, 70, 46.
6.Helmchen, G; Hoffmann, R. W; Mulzer, J; Schaumann, E; Eds, Houben-Weyl, Stereoselective Synthesis, 1995.
7.(a) Morrison, J. D. Ed, Asymmetric Synthesis Vol. 1-5, Academic, New York, 1983. (b) Blaser, H. U. Chem. Rev. 1992, 92, 935
8.(a) Ojima, I. Ed. Catalytic Asymmetric Synthesis, VCH, Weinheim, 1993. (b) Jacobson, E, N, Pfaltz, A.; Yamamoto, H. Eds. Comprehensive Asymmetric Catalysis I-III, Springer, Berlin, 1999. (c) Ojima, I. Ed. Catalytic Asymmetric Synthesis, 2nd ed, Wiley-VCH, New York, 2000. (d) Lin, G. Q.; Li, Y. M.; Chan, Albert S. C. Eds. Principles And Application of Asymmetric Synthesis, Wiley- Interscience, New York, 2001.
9.(a) Knowles, W. S.; Sabacky, M. J. J. Chem. Soc., Chem. Commun. 1968, 1445. (b) Noyori, R. Science 1990, 248, 1194. (c) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
10.黃全德博士論文，國立清華大學化學系，1999年。
11.Wu, H.-L.; Uang, B.-J. Tetrahedron: Asymmetry 2002, 13, 2625.
12.吳學亮博士論文，國立清華大學化學系，2004年。
13.Wu, P. -Y.; Wu, H. -L.; Uang, B. -J. J. Org. Chem. 2006, 71, 833.
14.Corey, E. J.; Cimprich, K. A. J. Am. Chem. Soc. 1994, 116, 3151.
15.(a) Chan, A. S. C.; Lu, G.; Li, X.; Chan, W. L. Chem. Commun. 2002, 172. (b) Chan, A. S. C.; Lu, G.; Li, X.; Kwok, W. H. J. Am. Chem. Soc. 2002, 124, 12636.
16.(a) Moore, D.; Pu, L. Org. Lett. 2002, 4, 1855. (b) Xu, M. -H.; Pu, L. Org. Lett. 2002, 4, 4555.
17.(a) Frantz, D. E.; Fassler, R.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 1806. (b) Frantz, D. E.; Fassler, R.; Tomooka, C, S,; Carreira, E. M. Acc. Chem. Res. 2000, 33, 373. (c) Boyall, D.; Lopez, F.; Sasaki, H.; Frantz, D.; Carreira, E. M. Org. Lett. 2000, 2, 4233. (d) EI-Sayed, E.; Anand, N. K.; Carreira, E. M. Org. Lett. 2001, 3, 3017.
18.(a) Gao, G.; Moore, D.; Pu, L. Org. Lett. 2002, 4, 4143. (b) Li, Z. B.; Pu, L. Org. Lett. 2004, 6, 1065.
19.Emmerson, D. P. G.; Hems, W. P.; Davis, B. G. Org. Lett. 2006, 8, 207.
20.Boyall, D.; Frantz, D. E.; Carreira, E. M. Org. Lett. 2002, 4, 2605.
21.Rozners, E.; Xu, Q. Org. Lett. 2003, 5, 3999.
22.Anand, N. K.; Carreira, E. M. J. Am. Chem. Soc. 2001, 123, 9687.
23.Jiang, B.; Chen, Z.; Tang, X. Org. Lett. 2002, 4, 3451
24.吳志龍碩士論文，國立清華大學化學系，2005年。
25.溫岩芳博士論文，國立清華大學化學系，2003年。
26.葉財龍博士論文，國立清華大學化學系，1992年。
27.Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033.
28.Arnold, L. A.; Imbos, R.; Mandoli, A.; de Vries, A. H. M.; Naasz, R.; Feringa, B. L. Tetrahedron 2000, 56, 2865.
29.(a) Alexakis, A.; Burton, J.; Vastra, J.; Benhaim, C.; Fournioux, X.; Heuvel, A. V. D.; Leveque, J.-M.; Maze, F.; Rosset, S. Eur. J. Org. Chem. 2000, 4011 (b) Pamies, O.; Net, G.; Ruiz, A.; Claver, C. Tetrahedron: Asymmetry 1999, 10, 2007. (c) Yan, M.; Chan, A. S. C. Tetrahedron Lett. 1999, 40, 6645.
30.(a) Escher, I. H.; Pfalz, A. Tetrahedron 2000, 56, 2879. (b) Delapierre, G.; Constantieux, T.; Brunel, J. M.; Buono, G. Eur. J. Org. Chem. 2000, 2507. (c) Hu, X.; Chen, H.; Zhang, X. Angew. Chem. Int. Ed. 1999, 38, 3518.
31.(a) Kitamura, M.; Miki, T.; Nakano, K.; Noyori, R. Tetrahedron Lett. 1996, 37, 5141. (b) Wendisch, V.; Sewald, N. Tetrahedron: Asymmetry 1997, 8, 1253. (c) Chataigner, I.; Gennari, C.; Piarulli, U.; Ceccarelli, S. Angew. Chem. Int. Ed. 2000, 39, 916. (d) Garcia, C. ; LaRochelle, L. K. ; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10970.
32.Chataigner, I.; Gennari, C.; Ongeri, S.; Piarulli, U.; Ceccarelli, S. Chem. Eur. J. 2001, 7, 2628.
33.Huang, C.-D. ; Uang, B.-J. Tetrahedron: Asymmetry 1998, 9, 3979.
34.詹德品博士論文，國立清華大學化學系，2004年。
35.楊以仁博士論文，國立清華大學化學系，2005年。
36.呂和榮碩士論文，國立清華大學化學系，2005年。
37.Ramon, D. J.; Yus, M. Tetrahedron: Asymmetry 1997, 8, 2479.