Asymmetric (3+2) Cycloaddition Employing β‐Fluoroalkylated α,β‐Unsaturated 2‐Acyl Imidazole Catalyzed by a Chiral‐at‐Metal Rhodium Complex

Abstract

AbstractAn asymmetric 1,3‐dipolar cycloaddition of β‐fluoroalkylated α,β‐unsaturated 2‐acyl imidazole with nitrones or N,N’‐cyclic azomethine imines to construct chiral α‐fluoroalkylated γ‐amino alcohols or chiral α‐fluoroalkylated 1,3‐diamino compounds has catalyzed by chiral‐at‐metal rhodium complexes is reported. The corresponding products with three contiguous tertiary stereocenters were obtained in 62%–98% yields with stereoselectivities up to >20:1 dr and 99% ee. Remarkably, as low as 0.06 mol% of chiral‐at‐metal rhodium complex can promote a gram‐scale reaction with nitrones or N,N’‐cyclic azomethine imines.