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

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

A new class of axial-chiral biisoquinoline <i>N</i>,<i>N′</i>-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 re...

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Bibliographic Details
Main Authors: Shiyu Sun, Changgong Xu, Jamielyn Jarvis, Phillip Nader, Brandon Naumann, Abigail Soliven, Roberto Peverati, Norito Takenaka
Format: Article
Language:English
Published: MDPI AG 2021-09-01
Series:Catalysts
Subjects:
Lewis base catalysis
trichlorosilane
hydrosilylation
hydrazone
computational chemistry
Online Access:https://www.mdpi.com/2073-4344/11/9/1103
Description
Summary:A new class of axial-chiral biisoquinoline <i>N</i>,<i>N′</i>-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 (<b>2a</b>–HSiCl<sub>3</sub>) were analyzed using density functional theory calculations.
ISSN:2073-4344

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