Evaluation of 3,3′-Triazolyl Biisoquinoline <i>N</i>,<i>N′</i>-Dioxide Catalysts for Asymmetric Hydrosilylation of Hydrazones with Trichlorosilane

Abstract

A new class of axial-chiral biisoquinoline N,N′-dioxides was evaluated as catalysts for the enantioselective hydrosilylation of acyl hydrazones with trichlorosilane. While these catalysts provided poor to moderate reactivity and enantioselectivity, this study represents the first example of the organocatalytic asymmetric reduction of acyl hydrazones. In addition, the structures and energies of two possible diastereomeric catalyst–trichlorosilane complexes (2a–HSiCl3) were analyzed using density functional theory calculations.

Keywords

• Lewis base catalysis
• trichlorosilane
• hydrosilylation
• hydrazone
• computational chemistry