Wittig-Type E-Selective Olefination of Imines with Vinyl Boronate Esters Under Copper Hydride Catalysis

Key words

alkenes - copper catalysis - imines - olefination - vinyl boronate esters

Significance

Lalic and co-workers report a novel copper hydride-catalyzed protocol for the stereoselective Wittig-type olefination of imines with vinyl boronate esters. This versatile strategy features broad functional-group compatibility and tolerates both aryl and alkyl imines, providing the corresponding alkenes with high E-selectivities.

Comment

Mechanistic investigations including control experiments and NMR studies support the shown catalytic cycle. The reaction’s success relies on the heterobimetallic intermediate, which serves as an ylide equivalent. The high E-selectivity is based on the stereoselective addition of that intermediate to the imine, followed by a stereospecific anti-elimination.

Publication History

Article published online:
14 February 2024