Nickel(II)‐Catalyzed Enantioselective 1,3‐Dipolar Cycloaddition of Nitrones with α,β‐Unsaturated Acylcarboxylates

Abstract

The highly enantioselective 1,3‐dipolar cycloaddition of nitrones with α,β‐unsaturated acylcarboxylates was realized for the first time by using a chiral bis(indano‐oxazoline)‐based Ni complex. The reaction proceeded smoothly under mild conditions and provided isoxazolidines with three contiguous stereocenters in high yields with excellent diastereoselectivities (>20:1 dr) and enantioselectivities (up to 99 % ee). The reaction was scaled up to the gram scale, and the products were readily transformed into γ‐amino alcohols and other potentially bioactive compounds.