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

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 H-2 as the sole byproduct. Key to the success for discrimination of the gem-diol groups in silanediol relies on an enantioselective sigma-bond metathesis process. Further straightforward elaboration of the enantioenriched silicon-stereogenic silanols delivers several interesting chiral silane scaffolds without the loss of enantiopurities.

Automated summary

This study demonstrates a copper-catalyzed asymmetric synthesis of silanediols, which allows for the synthesis of various functionalized chiral silanols. The method exhibits high atom economy, decent yield with excellent stereoselectivity, and H-2 as the sole byproduct.