Catalytic Asymmetric Aldol Reactions. Use of a Chiral (Acyloxy)borane Complex as a Versatile Lewis Acid Catalyst

Journal of the American Chemical Society

Volumn 113, Issue 3, 1991, Pages 1041-1042

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

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1842741675     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00003a047     Document Type: Article

References (15)

1. Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3.
2. Paterson, I.; Goodman, J. M.; Lister, M. A.; Schumann, R. C.; McClure, C. K.; Norcross, R. D. Tetrahedron 1990, 46, 4663 and references cited therein. Recently, Mukaiyama et al. reported catalytic asymmetric aldol-type reactions of silyl ethers of propanethioate mediated by a chiral tin reagent.
3. Mukaiyama, T.; Kobayashi, S.; Uchiro, H.; Shiina, I. Chem. Lett. 1990, 129.
4. Kobayashi, S.; Fujishita, Y.; Mukaiyama, T. Chem. Lett. 1990, 1455.
5. For precedent applications of CAB catalysts to asymmetric reactions, see:
6. Furuta, K.; Miwa, Y.; Iwanaga, K.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 6254.
7. Furuta, K.; Shimizu, S.; Miwa, Y.; Yamamoto, H. J. Org. Chem. 1989, 54, 1481.
8. Furuta, K.; Kanematsu, A.; Yamamoto, H.; Takaoka, S. Tetrahedron Lett. 1989, 30, 7231.
9. For a review of the Mukaiyama aldol reaction, see: Mukaiyama, T. Org. React. (N.Y.) 1982, 28, 203.
10. Tartaric acid 1 was prepared by the monoacylation of dibenzyl tartrate followed by hydrogenolysis.
11. The use of 10 mol % catalyst for the reaction resulted in a significant decrease in reactivity.
12. The reaction of a silyl ether of tert-butyl ethyl ketone (Z form) exceptionally gave the threo adduct predominantly (74/26 ratio). See ref 7.
13. Murata, S.; Suzuki, M.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 3248.
14. Noyon, R.; Murata, S.; Suzuki, M. Tetrahedron 1981, 37, 3899. In the case of the reaction of tert-butyl ethyl ketone (R1 = t-Bu, R2 = Me, Z form, in Figure 1), it could be considered that the steric repulsion between R and R1 (=t-Bu) in the erythro transition state becomes more significant than that between R and R2 in the threo transition state.
15. The superiority of propionitrile as a solvent for catalytic asymmetric aldol-type reactions has been reported: see ref 1d.