Efficient intramolecular asymmetric reductions of α-, β-, and γ-keto acids with diisopinocampheylborane1

Organic Letters

Volumn 3, Issue 1, 2001, Pages 17-18

  Veeraraghavan Ramachandran, P ^a   Brown, Herbert C ^a   Pitre, Sangeeta ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 HEXANOLIDE; 4-HEXANOLIDE; BORON DERIVATIVE; LACTONE; OXOACID; PHEROMONE;

ANIMAL; ARTICLE; BEETLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; FEMALE; SECRETION; SYNTHESIS;

ANIMALS; BEETLES; BORON COMPOUNDS; CATALYSIS; FEMALE; KETO ACIDS; LACTONES; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PHEROMONES;

EID: 0035843311     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0062291     Document Type: Article

References (12)

1. Contribution 7 from the Herben C. Brown Center for Borane Research.
2. (a) Collins, I. J. Chem. Soc., Perkin Trans. 1 1999, 1377.
3. (b) Wang, Z.; Meng, X. J.; Kabalka, G. W. Tetrahedron Lett. 1991 32, 4619.
4. (c) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97.
5. (a) DIP-Chloride is the trademark of the Alclrich Chemical Co.
6. (b) Ramachandran, P. V.; Chen, G. M.; Brown, H. C. Tetrahedron Lett. 1996, 37, 2205.
7. (a) Wang, Z.; La, B.; Fortunak, J. M.; Meng, X. J.; Kabalka, G. W. Tetrahedron Lett. 1998 39, 5501.
8. (b) Wang, Z.; Zhao, C.; Pierce, M. E.; Fortunak, J. M. Tetrahedron: Asymmetry 1999, 10, 225.
9. The % ee and configuration are based on the optical rotation reported in the literature. Brown, H. C.; Kulkarni, S. V.; Racherla, U. S. J. Org. Chem. 1994, 59, 365.
10. (a) Mori, K.; Mori, H.; Sugai, T. Tetrahedron 1985, 41, 919 and references therein.
11. (b) It has been shown that T. granarium responds to (R)-9 only and not to its antipode or a racemic mixture.
12. Jakovac, I. J.; Jones, J. B. J. Org. Chem. 1979, 44, 2165.