Copper-Catalyzed Desymmetrization of Prochiral Silanediols to Silicon-Stereogenic Silanols

Abstract

Despite the growing demand for the enantioenriched silicon-stereogenic silanols in materials science, medicinal chemistry, and modern synthetic chemistry, the catalytic asymmetric synthesis of which remains a considerable challenge compared with their carbinol analogues. Herein, a copper-catalyzed desymmetrization of silanediols for the synthesis of various functionalized chiral silanols is demonstrated. The reaction features high atom economy, decent yield with excellent stereoselectivity, and H2 as the sole byproduct. Key to the success for discrimination of the gem-diol groups in silanediol relies on an enantioselective σ-bond metathesis process. Further straightforward elaboration of the enantioenriched silicon-stereogenic silanols delivers several interesting chiral silane scaffolds without the loss of enantiopurities.