Comprehensive　Summary　Silyl　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　beta-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　alpha-silylated　esters.　The　synthetic　versatility　of　the　boron-silicon　bifunctional　products　was　demonstrated　by　down-stream　transformations.