Bimetallic tandem catalysis-enabled enantioselective cycloisomerization/carbonyl–ene reaction for construction of 5-oxazoylmethyl α-silyl alcohol
Xinpeng Sang, Yuhao Mo, Shiya Li, Xiaohua Liu, Weidi Cao, Xiaoming Feng
Abstract
-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.
Topics & Concepts
CycloisomerizationBimetallic stripEnantioselective synthesisEne reactionTandemChemistryAlcoholCatalysisStereochemistryOrganic chemistryMaterials scienceComposite materialAsymmetric Synthesis and CatalysisCyclopropane Reaction MechanismsAsymmetric Hydrogenation and Catalysis