Chiral (Acyloxy)borane catalyzed asymmetric aldol type reaction of ketene silyl acetals with aldehydes

Synlett

Volumn 1991, Issue 6, 1991, Pages 439-440

  Furuta, Kyoji ^a   Maruyama, Tohru ^a   Yamamoto, Hisashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003788192     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-1991-20756     Document Type: Article

References (33)

1. For precedent applications of CAB catalysts to asymmetric reactions, see:
2. Furuta, K.; Miwa, Y.; Iwanaga, K.; Yamamoto, H. /. Am. Chem. Soc. 1988,110,6254.
3. Furuta, K.; Shimizu, S.; Miwa, Y.; Yamamoto, H. /. Org. Chem. 1989, 54, 1481.
4. Furuta, K.; Kanematsu, A.; Yamamoto, H.; Takaoka, S. Tetrahedron Lett. 1989,30,7231.
5. Furuta, K.; Maruyama, T.; Yamamoto, H. /. Am. Chem. Soc. 1991,113, 1041.
6. For chiral Lewis acid catalyzed asymmetric aldol type reactions of achiral ketene silyl acetals:
7. Mukaiyama, T.; Kobayashi, S.; Uchiro, H.; Shiina, I. Chem. Lett. 1990, 129.
8. Mukaiyama, T.; Kobayashi, S.; Sano, T. Tetrahedron 1990,46. 4653.
9. Mukaiyama, T.; Uchiro, H.; Kobayashi, S. Chem. Lett. 1990, 1147.
10. Kobayashi, S.; Fujishita, Y.; Mukaiyama, T. Chem. Lett. 1990, 1455.
11. Mukaiyama, T.; Takashima, T.; Kusaka, H.; Shimpuku, T. Chem. Lett. 1990,1777. For achiral Lewis acid catalyzed asymmetric aldol reactions of chiral ketene acetals:
12. Gennari, G; Bernardi, A.; Colombo, L.; Scolastico, C. /. Am. Chem. Soc. 1985,707, 5812.
13. Helmchen, G.; Leikauf, U.; Taufer-Knopfel, I. Angew. Chem. Int. Ed. Engl. 1985,24, 874.
14. Palazzi, C; Colombo, L.; Gennari, C. Tetrahedron Lett. 1986,27, 1735.
15. Gennari, C; Colombo, L.; Bertolini, G.; Schimperna, G. /. Org. Chem. 1987,52, 2754
16. Gennari, C; Molinari, P.; Cozzi, P.; Oliva, A. Tetrahedron Lett. 1989,30, 5163. Asymmetric aldol reactions using chiral enolates have been fully established. See
17. Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3. 0
18. Braun, M. Angew. Chem. Int. Ed. Engl. 1987, 26, 24.
19. Bonner, P.; Thornton, E. R. /. Am. Chem. Soc. 1991,113,1299 and references cited therein.
20. Reetz, M. T.; Kunisch, R; Heitmann, P. Tetrahedron Lett. 1986, 27, 4721.
21. In sharp contrast to the present results, TiCU and other related Lewis acids catalyzed reactions of ketene silyl acetals with aldehydes were reported to afford threo aldols in preference to erythro. Actually, the reaction of ketene silyl acetal derived from phenyl propionate with benzaldehyde catalyzed by TiCU resulted in the predominant formation of threo adduct (threo/erythro = 65/35). For discussions on stereochemistry of Lewis acid catalyzed aldol reactions of silyl ethers, see:
22. Reference 2k.
23. Gennari, C; Bernardi, A.; Cardani, S.; Scolastico, C. Tetrahedron Lett. 1985,26, 797.
24. Heathcock, C. H.; Davidsen, S. K.; Hug, K. T.; Flippin, L. A. /. Org. Chem. 1986,57, 3027.
25. Masamune, S.; Choy, W.; Kerdesky, F. A. J.; Imperiali, B. J. Am. Chem. Soc. 1981,703, 1566.
26. Evans, D. A.; Bartroli, J.; Shih, T. L. /. Am. Chem. Soc. 1981, 703, 2127.
27. Evans, D. A.; McGee, L. R. /. Am. Chem. Soc. 1981,703, 2876.
28. Meyers, A. I.; Yamamoto, Y. /. Am. Chem. Soc. 1981, 703, 4278.
29. Helmchen, G.; Leikauf, U.; Taufer-Knepfel, I. Angew. Chem. Int. Ed. Engl. 1985,24, 874.
30. Masamune, S.; Sato, T.; Kim, B-M.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 70S, 8279.
31. Gennari, C; Colombo, L.; Bertolini, G.; Schimperna, G. /. Org. Chem. 1987,52, 2754.
32. Riediker, M.; Duthaler, R. O. Angew. Chem. Int. Ed. Engl. 1989,28, 495.
33. Oppolzer, W.; Blagg, J.; Rodriguez, I.; Walther, E. /. Am. Chem. Soc. 1990,772, 2767.