Phosphine‐Catalyzed Enantioselective (3+2) Annulation of Vinylcyclopropanes with Imines for the Synthesis of Chiral Pyrrolidines

作者：Zhang Fuhao; Dai Xuan; Dai Lei; Zheng Wenrui; Chan WaiLun; Tang Xiaodong; Zhang Xumu; Lu Yixin

来源：Angewandte Chemie, 2022, 134(24).

DOI：10.1002/ANGE.202203212

• Annulation
• Enantioselective
• Phosphine Catalysis
• Pyrrolidines
• Vinylcyclopropanes

A phosphine‐catalyzed highly enantioselective and diastereoselective (up to 98?% ee and >20?:?1 dr) (3+2) annulation between vinylcyclopropanes and N‐tosylaldimines has been developed, which allows facile access to a range of highly functionalized chiral pyrrolidines. Notably, this method makes use of vinylcyclopropanes as a synthon for phosphine‐mediated asymmetric annulation reaction, which will offer new opportunities for potential applications of cyclopropanes substrates in phosphine‐catalyzed organic transformations.(#br)Cyclopropanes are important synthetic building blocks in organic chemistry. In this study, the first phosphine‐catalyzed enantioselective (3+2) annulation between vinylcyclopropanes and N‐tosylaldimines was achieved, which led to the formation of a range of highly functionalized pyrrolidines in high yields with excellent diastereo‐ and enantioselectivities.