Regio‐ and Diasteroselective C‐Silylation of Enolate Enabled by a β‐Boronyl Group

Abstract

Comprehensive SummarySilyl enol ethers are often obtained when the lithium enolates are trapped with chlorosilanes. Herein, we report a general method for the regio‐ and diasteroselective C‐silylation of enolate enabled by the β‐boronyl group. The formation of five‐membered chelation intermediate is key to the C‐selective silylation and anti‐selectivity. The operationally simple protocol provides a general and predictable access to the α‐silylated esters. The synthetic versatility of the boron–silicon bifunctional products was demonstrated by down‐stream transformations.