Construction of Chiral Tetraorganosilicons by Tandem Desymmetrization of Silacyclobutanes/Intermolecular Dehydrogenative Silylation

Qing-Wei Zhang; Kun An; Li-Chuan Liu; Qi Zhang; Huifang Guo; Wei He

doi:10.1002/anie.201609022

Construction of Chiral Tetraorganosilicons by Tandem Desymmetrization of Silacyclobutanes/Intermolecular Dehydrogenative Silylation

Angew Chem Int Ed Engl. 2017 Jan 19;56(4):1125-1129. doi: 10.1002/anie.201609022. Epub 2016 Dec 19.

Authors

Qing-Wei Zhang¹, Kun An¹, Li-Chuan Liu¹, Qi Zhang¹, Huifang Guo¹, Wei He¹

Affiliation

¹ School of Pharmaceutical Sciences, Tsinghua University, Beijing, 100084, China.

PMID: 27990736
DOI: 10.1002/anie.201609022

Abstract

We report a method to construct chiral tetraorganosilicons by tandem silacyclobutane (SCB) desymmetrization-dehydrogenative silylations. A wide array of dibenzosiloles with stereogenic quaternary silicon centers were obtained in good yields and enantioselectivities up to 93 % ee. Chiral TMS-segphos was found to be a superior ligand in terms of reactivity and enantioselectivity.

Keywords: dibenzosiloles; enantioselectivity; silacyclobutanes; tetraorganosilicons.

Publication types

Research Support, Non-U.S. Gov't