Catalytic asymmetric synthesis of diazabicyclo[3.1.0]hexanes by 1,3-dipolar cycloaddition of azomethine ylides with azirines

Abstract

Substituted 1,3-diazabicyclo[3.1.0]hexanes with two contiguous quaternary stereocentres are readily prepared by catalytic asymmetric [3+2] cycloaddition of α-substituted iminoesters with azirines. High diastereoselectivities and enantioselectivities (up to 98% ee) are achieved using Cu^I/(R)-Fesulphos as the catalytic system.