Abstract
Catalytic asymmetric addition reactions of enecarbamates with ethyl glyoxylate have been developed using CuClO 4·4CH 3CN and a diimine ligand as the catalyst. Highly diastereo- and enantioselective addition reactions of α-mono-substituted enecarbamates have been also achieved. These reactions afforded the corresponding adducts with high selectivity; that is, syn adducts from Z-enecarbamates and anti adducts from E-enecarbamates. The proposed reaction mechanism is an aza-ene type pathway, where the proton of an enecarbamate's N–H group plays an important role, not only for accelerating the reaction but also for providing a transition state suitable for the highly selective chiral induction.
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