Organosilanes in copper-mediated conjugate reductions and reductive aldol reactions

Synthesis

Volumn , Issue 13, 2004, Pages 2210-2215

  Chiu, Pauline ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

Aldol reactions; Copper conjugate reductions; Organosilanes

Indexed keywords

CATALYSTS; COPPER COMPOUNDS; OLEFINS; ORGANIC COMPOUNDS; TRANSITION METALS;

CYCLIZATION; ORGANOSILANES; TRANSITION METAL CATALYSTS;

SILANES;

1 ACETYL 8A HYDROXY 6 METHYL 4,7,8,8A TETRAHYDRO 3H AZULENE 3A CARBOXYLIC ACID ETHYL ESTER; ALKENE DERIVATIVE; COPPER; COPPER DERIVATIVE; COPPER HYDRIDE; ORGANOSILANE DERIVATIVE; SILANE DERIVATIVE; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ALDOL REACTION; ALKYLATION; ARTICLE; CATALYSIS; CATALYST; CONJUGATION; CYCLIZATION; ENANTIOSELECTIVITY; REACTION ANALYSIS; REDUCTION; STOICHIOMETRY;

EID: 4544221000     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-831172     Document Type: Article

References (34)

1. (a) Ojima, I. Catalytic Asymmetric Synthesis; VCH: New York, 1993, Chap 6.
2. (b) Larock, R. C. Comprehensive Organic Transformations, 2nd ed; Wiley-VCH: New York, 1999, 13-26.
3. For a review on the complementary hydrosilylation of carbonyl compounds by organosilanes, see: Carpentier, J. F.; Bette, V. Curr. Org. Chem. 2002, 6, 913.
4. Mahoney, W. S.; Brestensky, D. M.; Stryker, J. M. J. Am. Chem. Soc. 1988, 110, 291.
5. Mori, A.; Fujita, A.; Nishihara, Y.; Hiyama, T. Chem. Commun. 1997, 2159.
6. Ito, H.; Ishizuka, T.; Arimoto, K.; Miura, K.; Hosomi, A. Tetrahedron Lett. 1997, 38, 8887.
7. (a) Lipshutz, B. H.; Keith, J.; Papa, P.; Vivian, R. Tetrahedron Lett. 1998, 39, 4627.
8. (b) Lipshutz, B. H.; Chrisman, W.; Noson, K.; Papa, P.; Sclafani, J. A.; Vivian, R. W.; Keith, J. M. Tetrahedron 2000, 56, 2779.
9. (a) Appella, D. H.; Moritani, Y.; Shintani, R.; Ferreira, E. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9473.
10. (b) Moritani, Y.; Appella, D. H.; Jurkauskas, V.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 6797.
11. (c) Lipshutz, B. H.; Servesko, J. M. Angew. Chem. Int. Ed. 2003, 42, 4789.
12. (d) Hughes, G.; Kimura, M.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 11253.
13. (e) Czekelius, C.; Carreira, E. M. Angew. Chem. Int. Ed. 2003, 42, 4793.
14. (a) Mahoney, W. S.; Stryker, J. M. J. Am. Chem. Soc. 1989, 111, 8818.
15. (b) Goeden, G. V.; Caulton, K. G. J. Am. Chem. Soc. 1981, 103, 7354.
16. (c) Brestensky, D. M.; Huseland, D. E.; McGettigan, C.; Stryker, J. M. Tetrahedron Lett. 1988, 29, 3749.
17. Chiu, P.; Li, Z.; Fung, K. C. M. Tetrahedron Lett. 2003, 44, 455.
18. p-Tol-BINAP: 2,2′-bis(di-p-tolylphosphino)-1,1′-binaphthyl; BIPHEMP: 2,2′-bis(diphenylphosphino)-6,6′-dimethyl-1,1′- biphenyl; JOSIPHOS: 1-[2-diphenyl]-phosphanyl]ferrocenyl]ethyldicyclohexyl- phosphane; BINAP: 2,2′-bis(dipenylphosphino)-1,1′-binaphthyl; DuPhos: 1,2-bis(2,5)-dimethylphosphalano)benzene, pybox: 2,6-bis(oxazolinyl) pyridine.
19. Yun, J.; Buchwald, S. L. Org. Lett. 2001, 3, 1129.
20. Revis, A.; Hilty, T. K. Tetrahedron Lett. 1987, 28, 4809.
21. Matsuda, I.; Takahasi, K.; Sato, S. Tetrahedron Lett. 1990, 31, 5331.
22. Taylor, S. J.; Morken, J. P. J. Am. Chem. Soc. 1999, 121, 12202.
23. Kiyooka, S.; Shimizu, A.; Torii, S. Tetrahedron Lett. 1998, 39, 5237.
24. (a) Taylor, S. J.; Duffey, M. O.; Morken, J. P. J. Am. Chem. Soc. 2000, 122, 4528.
25. (b) Zhao, C. X.; Bass, J.; Morken, J. P. Org. Lett. 2001, 3, 2839.
26. (c) Zhao, C. X.; Duffey, M. O.; Taylor, S. J.; Morken, J. P. Org. Lett. 2001, 3, 1829.
27. Isayama, S.; Mukaiyama, T. Chem. Lett. 1989, 2005.
28. (a) Baik, T. G.; Luis, A. L.; Wang, L. C.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 5112.
29. (b) Wang, L. C.; Jang, H. Y.; Baik, T. G.; Luis, A. L.; Lynch, V.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 9448.
30. (c) Huddleston, R. R.; Krische, M. J. Synlett 2003, 12.
31. (a) Chiu, P.; Chen, B.; Cheng, K. F. Tetrahedron Lett. 1998, 39, 9299.
32. (b) Chiu, P.; Szeto, C. P.; Geng, Z.; Cheng, K. F. Tetrahedron Lett. 2001, 42, 4091.
33. (c) Chiu, P.; Szeto, C. P.; Geng, Z.; Cheng, K. F. Org. Lett. 2001, 3, 1901.
34. Chiu, P.; Leung, S. K. Chem. Commun. 2004, in press.