Reduction of 2-alkyl-2-carbomethoxy-cyclopentanone derivatives with sodium borohydride. Part 2. The elucidation of the diastereoselective control

Synthetic Communications

Volumn 27, Issue 18, 1997, Pages 3241-3257

  Teixeira, Lis H P ^a   Barreiro, Eliezer J ^a   Fraga, Carlos A M ^a  

^a FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANONE DERIVATIVE; SODIUM BOROHYDRIDE;

ALKYLATION; ARTICLE; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030754572     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919708004185     Document Type: Article

References (13)

1. Benetti, S. & Romagnoli, R., Chem. Rev., 1995, 95, 1065-1114.
2. Fraga, C. A. M. & Barreiro, E. J., Synth. Comm., 1995, 25, 1133-1144.
3. Barreiro, E. J. & Garcia, V. L., An. Acad. Brasil. Ciênc., 1985, 57, 417-425.
4. Fraga, C. A. M.; Miranda, A. L. P. & Barreiro, E. J., Chem. Pharm. Bull., 1996, 44, 2157-2161.
5. th Annual Meeting of Brazilian Chemical Society, QO-014.
6. Sant'Anna, C. M. R.; Alencastro, R. B.; Barreiro, E. J. & Fraga, C. A. M., J. Mol. Structure (TheoChem), 1995, 340, 193-199.
7. Jones, G. B. & Chapman, B. J., Synthesis, 1995, 475-497.
8. Purchase from Aldrich Chemical Co., Milwaukee, Wis., USA.
9. For a new methodology to preparation of cyclic β-ketoesters, see: Peçanha, E. P.; Fraga, C. A. M. & Barreiro, E. J. QuiÆmica Nova, 1997, 26, in press.
10. Barco, A., Benetti, S. & Pollini, G. P. Synthesis, 1976, 316-318.
11. For a recent papers about the diastereoselective reduction β-keto esters with sodium borohydride, see: a) Fujii, H., Oshima, K. & Utimoto, K., Tetrahedron Letters, 1991, 32, 6147-6150; b) Taniguchi, M., Fujii, H., Oshima, K. & Utimoto, K., Tetrahedron, 1993, 49, 11169-11182.
12. For a recent papers about the diastereoselective reduction β-keto esters with sodium borohydride, see: a) Fujii, H., Oshima, K. & Utimoto, K., Tetrahedron Letters, 1991, 32, 6147-6150; b) Taniguchi, M., Fujii, H., Oshima, K. & Utimoto, K., Tetrahedron, 1993, 49, 11169-11182.
13. Teixeira, L. H. P., Barreiro, E. J. & Fraga, C. A. M., 1997, unpublished results.