Chiral Lewis acid-catalyzed enantioselective intramolecular carbonyl ene reactions of unsaturated α-keto esters

Organic Letters

Volumn 5, Issue 20, 2003, Pages 3749-3752

  Yang, Dan ^a   Yang, Min ^a   Zhu, Nian Yong ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; ESTER; LEWIS ACID;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; REACTION ANALYSIS; ROOM TEMPERATURE;

EID: 0142106406     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035486d     Document Type: Article

References (39)

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5. For recent examples, see: (c) Mauruoka, K.; Hoshino, Y.; Shirasaka, T.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 3967-3970. (d) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949-3954. (e) Qian, C.; Huang, T. Tetrahedron Lett. 1997, 38, 6721-6724. (f) Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824-5825. (g) Gao, Y.; Lane-Bell, P.; Vederas, J. C. J. Org. Chem. 1998, 63, 2133-2143. (h) Gethergood, N.; Jørgensen, K. A. Chem. Commun. 1999, 1869-1870. (i) Reichel, F.; Fang, X.; Yao, S.; Ricci, M.; Jørgensen, K. A. Chem. Commun. 1999, 1505-1506. (j) Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936-7943. (k) Hao, J.; Hatano, M.; Mikami, K. Org. Lett. 2000, 2, 4059-4062. (l) Koh, J. H.; Larsen, A. O.; Gagne, M. R. Org. Lett. 2001, 3, 1233-1236. (m) Kezuka, S.; Ikeno, T.; Yamada, T. Org. Lett. 2001, 3, 1937-1939. (n) Becker, J. J.; van Orden, L. J.; White, P. S.; Gagne, M. R. Org. Lett. 2002, 4, 727-730.
6. For recent examples, see: (c) Mauruoka, K.; Hoshino, Y.; Shirasaka, T.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 3967-3970. (d) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949-3954. (e) Qian, C.; Huang, T. Tetrahedron Lett. 1997, 38, 6721-6724. (f) Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824-5825. (g) Gao, Y.; Lane-Bell, P.; Vederas, J. C. J. Org. Chem. 1998, 63, 2133-2143. (h) Gethergood, N.; Jørgensen, K. A. Chem. Commun. 1999, 1869-1870. (i) Reichel, F.; Fang, X.; Yao, S.; Ricci, M.; Jørgensen, K. A. Chem. Commun. 1999, 1505-1506. (j) Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936-7943. (k) Hao, J.; Hatano, M.; Mikami, K. Org. Lett. 2000, 2, 4059-4062. (l) Koh, J. H.; Larsen, A. O.; Gagne, M. R. Org. Lett. 2001, 3, 1233-1236. (m) Kezuka, S.; Ikeno, T.; Yamada, T. Org. Lett. 2001, 3, 1937-1939. (n) Becker, J. J.; van Orden, L. J.; White, P. S.; Gagne, M. R. Org. Lett. 2002, 4, 727-730.
7. For recent examples, see: (c) Mauruoka, K.; Hoshino, Y.; Shirasaka, T.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 3967-3970. (d) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949-3954. (e) Qian, C.; Huang, T. Tetrahedron Lett. 1997, 38, 6721-6724. (f) Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824-5825. (g) Gao, Y.; Lane-Bell, P.; Vederas, J. C. J. Org. Chem. 1998, 63, 2133-2143. (h) Gethergood, N.; Jørgensen, K. A. Chem. Commun. 1999, 1869-1870. (i) Reichel, F.; Fang, X.; Yao, S.; Ricci, M.; Jørgensen, K. A. Chem. Commun. 1999, 1505-1506. (j) Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936-7943. (k) Hao, J.; Hatano, M.; Mikami, K. Org. Lett. 2000, 2, 4059-4062. (l) Koh, J. H.; Larsen, A. O.; Gagne, M. R. Org. Lett. 2001, 3, 1233-1236. (m) Kezuka, S.; Ikeno, T.; Yamada, T. Org. Lett. 2001, 3, 1937-1939. (n) Becker, J. J.; van Orden, L. J.; White, P. S.; Gagne, M. R. Org. Lett. 2002, 4, 727-730.
8. For recent examples, see: (c) Mauruoka, K.; Hoshino, Y.; Shirasaka, T.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 3967-3970. (d) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949-3954. (e) Qian, C.; Huang, T. Tetrahedron Lett. 1997, 38, 6721-6724. (f) Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824-5825. (g) Gao, Y.; Lane-Bell, P.; Vederas, J. C. J. Org. Chem. 1998, 63, 2133-2143. (h) Gethergood, N.; Jørgensen, K. A. Chem. Commun. 1999, 1869-1870. (i) Reichel, F.; Fang, X.; Yao, S.; Ricci, M.; Jørgensen, K. A. Chem. Commun. 1999, 1505-1506. (j) Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936-7943. (k) Hao, J.; Hatano, M.; Mikami, K. Org. Lett. 2000, 2, 4059-4062. (l) Koh, J. H.; Larsen, A. O.; Gagne, M. R. Org. Lett. 2001, 3, 1233-1236. (m) Kezuka, S.; Ikeno, T.; Yamada, T. Org. Lett. 2001, 3, 1937-1939. (n) Becker, J. J.; van Orden, L. J.; White, P. S.; Gagne, M. R. Org. Lett. 2002, 4, 727-730.
9. For recent examples, see: (c) Mauruoka, K.; Hoshino, Y.; Shirasaka, T.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 3967-3970. (d) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949-3954. (e) Qian, C.; Huang, T. Tetrahedron Lett. 1997, 38, 6721-6724. (f) Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824-5825. (g) Gao, Y.; Lane-Bell, P.; Vederas, J. C. J. Org. Chem. 1998, 63, 2133-2143. (h) Gethergood, N.; Jørgensen, K. A. Chem. Commun. 1999, 1869-1870. (i) Reichel, F.; Fang, X.; Yao, S.; Ricci, M.; Jørgensen, K. A. Chem. Commun. 1999, 1505-1506. (j) Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936-7943. (k) Hao, J.; Hatano, M.; Mikami, K. Org. Lett. 2000, 2, 4059-4062. (l) Koh, J. H.; Larsen, A. O.; Gagne, M. R. Org. Lett. 2001, 3, 1233-1236. (m) Kezuka, S.; Ikeno, T.; Yamada, T. Org. Lett. 2001, 3, 1937-1939. (n) Becker, J. J.; van Orden, L. J.; White, P. S.; Gagne, M. R. Org. Lett. 2002, 4, 727-730.
10. For recent examples, see: (c) Mauruoka, K.; Hoshino, Y.; Shirasaka, T.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 3967-3970. (d) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949-3954. (e) Qian, C.; Huang, T. Tetrahedron Lett. 1997, 38, 6721-6724. (f) Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824-5825. (g) Gao, Y.; Lane-Bell, P.; Vederas, J. C. J. Org. Chem. 1998, 63, 2133-2143. (h) Gethergood, N.; Jørgensen, K. A. Chem. Commun. 1999, 1869-1870. (i) Reichel, F.; Fang, X.; Yao, S.; Ricci, M.; Jørgensen, K. A. Chem. Commun. 1999, 1505-1506. (j) Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936-7943. (k) Hao, J.; Hatano, M.; Mikami, K. Org. Lett. 2000, 2, 4059-4062. (l) Koh, J. H.; Larsen, A. O.; Gagne, M. R. Org. Lett. 2001, 3, 1233-1236. (m) Kezuka, S.; Ikeno, T.; Yamada, T. Org. Lett. 2001, 3, 1937-1939. (n) Becker, J. J.; van Orden, L. J.; White, P. S.; Gagne, M. R. Org. Lett. 2002, 4, 727-730.
11. For recent examples, see: (c) Mauruoka, K.; Hoshino, Y.; Shirasaka, T.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 3967-3970. (d) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949-3954. (e) Qian, C.; Huang, T. Tetrahedron Lett. 1997, 38, 6721-6724. (f) Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824-5825. (g) Gao, Y.; Lane-Bell, P.; Vederas, J. C. J. Org. Chem. 1998, 63, 2133-2143. (h) Gethergood, N.; Jørgensen, K. A. Chem. Commun. 1999, 1869-1870. (i) Reichel, F.; Fang, X.; Yao, S.; Ricci, M.; Jørgensen, K. A. Chem. Commun. 1999, 1505-1506. (j) Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936-7943. (k) Hao, J.; Hatano, M.; Mikami, K. Org. Lett. 2000, 2, 4059-4062. (l) Koh, J. H.; Larsen, A. O.; Gagne, M. R. Org. Lett. 2001, 3, 1233-1236. (m) Kezuka, S.; Ikeno, T.; Yamada, T. Org. Lett. 2001, 3, 1937-1939. (n) Becker, J. J.; van Orden, L. J.; White, P. S.; Gagne, M. R. Org. Lett. 2002, 4, 727-730.
12. For recent examples, see: (c) Mauruoka, K.; Hoshino, Y.; Shirasaka, T.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 3967-3970. (d) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949-3954. (e) Qian, C.; Huang, T. Tetrahedron Lett. 1997, 38, 6721-6724. (f) Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824-5825. (g) Gao, Y.; Lane-Bell, P.; Vederas, J. C. J. Org. Chem. 1998, 63, 2133-2143. (h) Gethergood, N.; Jørgensen, K. A. Chem. Commun. 1999, 1869-1870. (i) Reichel, F.; Fang, X.; Yao, S.; Ricci, M.; Jørgensen, K. A. Chem. Commun. 1999, 1505-1506. (j) Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936-7943. (k) Hao, J.; Hatano, M.; Mikami, K. Org. Lett. 2000, 2, 4059-4062. (l) Koh, J. H.; Larsen, A. O.; Gagne, M. R. Org. Lett. 2001, 3, 1233-1236. (m) Kezuka, S.; Ikeno, T.; Yamada, T. Org. Lett. 2001, 3, 1937-1939. (n) Becker, J. J.; van Orden, L. J.; White, P. S.; Gagne, M. R. Org. Lett. 2002, 4, 727-730.
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