Transition-Metal-Free Synthesis of Enantioenriched Tertiary and Quaternary a-Chiral Allylsilanes

Access to enantioenriched tertiary and quaternary a-chiral allysilanes without any transition-metal catalyst is reported. This was achieved by enantioselective allylic displacement of ?-silylated allylic bromides through Lewis base activation of Grignard reagents by a bidentate chiral NHC ligand. The process afforded both high ?-regio- and enantioselectivity and is compatible with a wide range of silyl groups on the substrates.

Automated summary

Access to enantioenriched tertiary and quaternary α-chiral allysilanes without any transition-metal catalyst is achieved by enantioselective allylic displacement. This process involves Lewis base activation of Grignard reagents using a bidentate chiral NHC ligand and shows high β-regio- and enantioselectivity, while being compatible with various silyl groups on the substrates.