Synthetic communications

Reduction of 2-Alkyl-2-carbomethoxy-cyclopentanone Derivatives with Sodium Borohydride. II. The Elucidation of the Diastereoselective Control a

LHP Teixeira, EJ Barreiro, CAM Fraga

Index: Teixeira, Lis H. P.; Barreiro, Eliezer J.; Fraga, Carlos A. M. Synthetic Communications, 1997 , vol. 27, # 18 p. 3241 - 3257

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Citation Number: 20

Abstract

Abstract The synthesis and reduction of four new 2-substituted β-keto-ester derivatives (6– 9), employing inexpensive sodium borohydride, were achieved to evaluate the diastereoselectivity of the reduction process of 2-allyl-2-carbomethoxy cyclopentanone derivative (1a) in the same conditions. These results indicating that the diastereoselective control in this process depend on blockage of the re-face of (1a) by a proposed carbonyl-π ...