A Convenient Method for Asymmetric Reduction of Acetophenone using Lithium Hydroxide

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Abstract

Optically active lithium-alkoxide catalyzes asymmetric reduction of ketones and imines with alkoxyhydrosilane as a Lewis base. Lithium salt is generally formed by a mixture of optically active alcohol and n-butyllithium as a metal source, which is too sensitive to moisture to handle in air. However, if n-butyllithium is replaced by another lithium source which is stable in air, a more convenient reaction system results. In this study, we examined the enantioselective reduction of acetophenone using lithium hydroxide instead of n-butyllithium as the metal source. Similar reactivity of the reduction was obtained when tetrahydrofuran was the solvent. In contrast, enantioselectivites were lower than when n-butyllithium was used. These results indicate that the geometry of extracoordinated silicate as an active species is affected by the coordination of water molecules.

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