Chiral ketone catalyzed highly chemo- and enantioselective epoxidation of conjugated enynes

Journal of Organic Chemistry

Volumn 64, Issue 20, 1999, Pages 7646-7650

  Wang, Zhi Xian ^a   Cao, Guo An ^a   Shi, Yian ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; KETONE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; EPOXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033214816     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9907639     Document Type: Article

References (42)

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5. For some leading references on synthetic applications of alkynyloxiranes, see: (a) Alexakis, A.; Marek, I.; Mangeney, P.; Normant, J. F. Tetrahedron 1991, 47, 1677. (b) Marshall, J. A.; DuBay, W. J. J. Am. Chem. Soc. 1982, 114, 1450. (c) Marshall, J. A.; Pinney, K. G. J. Org. Chem. 1993, 58, 7180. (d) Marshall, J. A.; Tang, Y. J. Org. Chem. 1994, 59, 1457. (e) Mukai, C.; Sugimoto, Y-i.; Ikeda, Y.; Hanaoka, M. Tetrahedron Lett. 1994, 35, 2183. (f) Aurrecoechea, J. M.; Solay, M. Tetrahedron Lett. 1995, 36, 2501. (g) Piotti, M. E.; Alper, H. J. Org. Chem. 1997, 62, 8484. (h) Aurrecoechea, J. M.; Alonso, E.; Solay, M. Tetrahedron 1998, 64, 3833. (i) Aurrecoechea, J. M.; Solay, M. Tetrahedron 1998, 54, 3851. (j) Bernard, N.; Chemla, F.; Normant, J. F. Tetrahedron Lett. 1998, 39, 6715.
6. For some leading references on synthetic applications of alkynyloxiranes, see: (a) Alexakis, A.; Marek, I.; Mangeney, P.; Normant, J. F. Tetrahedron 1991, 47, 1677. (b) Marshall, J. A.; DuBay, W. J. J. Am. Chem. Soc. 1982, 114, 1450. (c) Marshall, J. A.; Pinney, K. G. J. Org. Chem. 1993, 58, 7180. (d) Marshall, J. A.; Tang, Y. J. Org. Chem. 1994, 59, 1457. (e) Mukai, C.; Sugimoto, Y-i.; Ikeda, Y.; Hanaoka, M. Tetrahedron Lett. 1994, 35, 2183. (f) Aurrecoechea, J. M.; Solay, M. Tetrahedron Lett. 1995, 36, 2501. (g) Piotti, M. E.; Alper, H. J. Org. Chem. 1997, 62, 8484. (h) Aurrecoechea, J. M.; Alonso, E.; Solay, M. Tetrahedron 1998, 64, 3833. (i) Aurrecoechea, J. M.; Solay, M. Tetrahedron 1998, 54, 3851. (j) Bernard, N.; Chemla, F.; Normant, J. F. Tetrahedron Lett. 1998, 39, 6715.
7. For some leading references on synthetic applications of alkynyloxiranes, see: (a) Alexakis, A.; Marek, I.; Mangeney, P.; Normant, J. F. Tetrahedron 1991, 47, 1677. (b) Marshall, J. A.; DuBay, W. J. J. Am. Chem. Soc. 1982, 114, 1450. (c) Marshall, J. A.; Pinney, K. G. J. Org. Chem. 1993, 58, 7180. (d) Marshall, J. A.; Tang, Y. J. Org. Chem. 1994, 59, 1457. (e) Mukai, C.; Sugimoto, Y-i.; Ikeda, Y.; Hanaoka, M. Tetrahedron Lett. 1994, 35, 2183. (f) Aurrecoechea, J. M.; Solay, M. Tetrahedron Lett. 1995, 36, 2501. (g) Piotti, M. E.; Alper, H. J. Org. Chem. 1997, 62, 8484. (h) Aurrecoechea, J. M.; Alonso, E.; Solay, M. Tetrahedron 1998, 64, 3833. (i) Aurrecoechea, J. M.; Solay, M. Tetrahedron 1998, 54, 3851. (j) Bernard, N.; Chemla, F.; Normant, J. F. Tetrahedron Lett. 1998, 39, 6715.
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9. For some leading references on synthetic applications of alkynyloxiranes, see: (a) Alexakis, A.; Marek, I.; Mangeney, P.; Normant, J. F. Tetrahedron 1991, 47, 1677. (b) Marshall, J. A.; DuBay, W. J. J. Am. Chem. Soc. 1982, 114, 1450. (c) Marshall, J. A.; Pinney, K. G. J. Org. Chem. 1993, 58, 7180. (d) Marshall, J. A.; Tang, Y. J. Org. Chem. 1994, 59, 1457. (e) Mukai, C.; Sugimoto, Y-i.; Ikeda, Y.; Hanaoka, M. Tetrahedron Lett. 1994, 35, 2183. (f) Aurrecoechea, J. M.; Solay, M. Tetrahedron Lett. 1995, 36, 2501. (g) Piotti, M. E.; Alper, H. J. Org. Chem. 1997, 62, 8484. (h) Aurrecoechea, J. M.; Alonso, E.; Solay, M. Tetrahedron 1998, 64, 3833. (i) Aurrecoechea, J. M.; Solay, M. Tetrahedron 1998, 54, 3851. (j) Bernard, N.; Chemla, F.; Normant, J. F. Tetrahedron Lett. 1998, 39, 6715.
10. For some leading references on synthetic applications of alkynyloxiranes, see: (a) Alexakis, A.; Marek, I.; Mangeney, P.; Normant, J. F. Tetrahedron 1991, 47, 1677. (b) Marshall, J. A.; DuBay, W. J. J. Am. Chem. Soc. 1982, 114, 1450. (c) Marshall, J. A.; Pinney, K. G. J. Org. Chem. 1993, 58, 7180. (d) Marshall, J. A.; Tang, Y. J. Org. Chem. 1994, 59, 1457. (e) Mukai, C.; Sugimoto, Y-i.; Ikeda, Y.; Hanaoka, M. Tetrahedron Lett. 1994, 35, 2183. (f) Aurrecoechea, J. M.; Solay, M. Tetrahedron Lett. 1995, 36, 2501. (g) Piotti, M. E.; Alper, H. J. Org. Chem. 1997, 62, 8484. (h) Aurrecoechea, J. M.; Alonso, E.; Solay, M. Tetrahedron 1998, 64, 3833. (i) Aurrecoechea, J. M.; Solay, M. Tetrahedron 1998, 54, 3851. (j) Bernard, N.; Chemla, F.; Normant, J. F. Tetrahedron Lett. 1998, 39, 6715.
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40. For leading references on the transition states of the dioxiranemediated epoxidation, see: (a) Baumstark, A. L.; McCloskey, C. J. Tetrahedron Lett. 1987, 28, 3311. (b) Baumstark, A. L.; Vasquez, P. C. J. Org. Chem. 1988, 53, 3437. (c) Bach, R. D.; Andres, J. L.; Owensby, A. L.; Schlegel, H. B.; McDouall, J. J. W. J. Am. Chem. Soc. 1992, 114, 7207. (d) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (e) Houk, K. N.; Liu, J.; DeMello, N. C.; Condroski, K. R. J. Am. Chem. Soc. 1997, 119, 10147. (f) Jenson, C.; Liu, J.; Houk, K. N.; Jorgensen, W. L. J. Am. Chem. Soc. 1997, 119, 12982.
41. For leading references on the transition states of the dioxiranemediated epoxidation, see: (a) Baumstark, A. L.; McCloskey, C. J. Tetrahedron Lett. 1987, 28, 3311. (b) Baumstark, A. L.; Vasquez, P. C. J. Org. Chem. 1988, 53, 3437. (c) Bach, R. D.; Andres, J. L.; Owensby, A. L.; Schlegel, H. B.; McDouall, J. J. W. J. Am. Chem. Soc. 1992, 114, 7207. (d) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (e) Houk, K. N.; Liu, J.; DeMello, N. C.; Condroski, K. R. J. Am. Chem. Soc. 1997, 119, 10147. (f) Jenson, C.; Liu, J.; Houk, K. N.; Jorgensen, W. L. J. Am. Chem. Soc. 1997, 119, 12982.
42. For leading references on the transition states of the dioxiranemediated epoxidation, see: (a) Baumstark, A. L.; McCloskey, C. J. Tetrahedron Lett. 1987, 28, 3311. (b) Baumstark, A. L.; Vasquez, P. C. J. Org. Chem. 1988, 53, 3437. (c) Bach, R. D.; Andres, J. L.; Owensby, A. L.; Schlegel, H. B.; McDouall, J. J. W. J. Am. Chem. Soc. 1992, 114, 7207. (d) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (e) Houk, K. N.; Liu, J.; DeMello, N. C.; Condroski, K. R. J. Am. Chem. Soc. 1997, 119, 10147. (f) Jenson, C.; Liu, J.; Houk, K. N.; Jorgensen, W. L. J. Am. Chem. Soc. 1997, 119, 12982.