N-Heterocyclic Carbene-Catalyzed Desymmetrization of Siladials To Access Silicon-Stereogenic Organosilanes
Hao Liu, Hongwei Zhou, Xingkuan Chen, Jianfeng Xu
Abstract
An N-heterocyclic carbene (NHC)-catalyzed enantioselective monoesterification of silicon-centered dialdehydes with alcohols or phenols is accomplished, providing optically active organosilanes bearing a stereogenic center at the silicon atom. This desymmetrization protocol is suitable for scale-up synthesis and late-stage modifications of complex molecules, and the products can be further transformed to other enantiopure functionalized silanes.
Topics & Concepts
DesymmetrizationStereocenterChemistryCarbeneSilanesEnantioselective synthesisEnantiopure drugCatalysisOrganic chemistryCombinatorial chemistrySilaneN-Heterocyclic Carbenes in Organic and Inorganic ChemistryCatalytic Cross-Coupling ReactionsSynthetic Organic Chemistry Methods