Bimetallic tandem catalysis-enabled enantioselective cycloisomerization/carbonyl-ene reaction for construction of 5-oxazoylmethyl α-silyl alcohol.

Abstract

A bimetallic tandem catalysis-enabled enantioselective cycloisomerization/carbonyl-ene reaction was developed. The reaction proceeded well with a broad range of N-propargylamides and acylsilanes, affording the target chiral 5-oxazoylmethyl α-silyl alcohols in up to 95% yield and 99% ee under mild conditions. Importantly, this facile protocol was available for the late-stage modification of several bioactive molecules. Based on the mechanistic study and control experiments, a possible catalytic cycle and transition state are proposed to elucidate the reaction process and enantioinduction.