Alkylmetal asymmetric reduction. 14. Enantioselective reduction of ketones by chiral (2-methylbutyl) aluminum derivatives

G Giacomelli, L Lardicci, F Palla…

Index: Giacomelli, Giampaolo; Lardicci, Luciano; Palla, Fabio; Caporusso, Anna Maria Journal of Organic Chemistry, 1984 , vol. 49, # 10 p. 1725 - 1728

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Citation Number: 8

Abstract

The reaction of tris [(S)-2-methylbutyl] aluminum with some a-alkynyl ketones has been studied: the organoaluminum derivative rapidly reduces the ketones to afford optically active a-alkynyl carbinols, which can be recovered after hydrolytic workup. The stereochemical results obtained are discussed on the basis of previous reports on enantioselective reductions of ketones by an alkylaluminum dichloride derived from 0-pinene. In this ...