Alkylmetal Asymmetric Reduction. 14. Enantioselective Reduction of Ketones by Chiral (2-Methylbutyl)aluminum Derivatives

Article abstract of DOI:10.1021/jo00184a011

The reaction of tris<(S)-2-methylbutyl>aluminum with some α-alkynyl ketones has been studied: the organoaluminum derivative rapidly reduces the ketones to afford optically active α-alkynyl carbinols, which can be recovered after hydrolytic workup.The sterochemical results obtained are discussed on the basis of previous reports on enantioselective reductions of ketones by an alkylaluminum dichloride derived from β-pinene.In this context, an investigation on the reaction between a series of ketones and β-branched alkylaluminum chlorides is also reported.