Intermolecular Catalytic Asymmetric Iodoetherification of Unfunctionalized Alkenes

A newly prepared trinuclear Zn-3-(R,S,S)-aminoiminobinaphthoxide complex (triZn-II) catalyzed the first general intermolecular asymmetric iodoetherification of unfunctionalized alkenes. Using triZn-II, the iodoetherification reaction of unfunctionalized alkenes with o-nitrophenols proceeded smoothly to give the products with up to 92.5:7.5 er, and diene substrates were converted to the products with up to 99:1 er with the formation of a meso-isomer (DL/meso = 78/22). The chiral iodoethers gave a new platform for the synthesis of chiral morpholines.

Automated summary

This study reports the asymmetric iodoetherification reaction of unfunctionalized alkenes and its catalyst triZn-II. The reaction shows high enantioselectivity and provides a new platform for the synthesis of chiral morpholines.