Azetidines are not only valuable core structures in many nature products, but also represent useful building blocks in organic synthesis and drug discovery. In contrast to the tremendous success in the catalytic asymmetric ring-opening reactions of epoxides, aziridines and oxetanes, those of azetidines are unprecedented due to the decreased reactivity especially for the 3-substituted azetidines. Inspired by our previous work, intermolecular desymmetrization of epoxides as well as oxetanes,1,2 we have developed an asymmetric ring-opening of azetidines. This process features broad functional group compatibility and high enantioselectivity as well as the capability to generate chiral quaternary centers. Details on the reaction conditions as well as the scope study will be presented.

Chiral Br�nsted acid catalyzed enantioselective intermolecular desymmetrizations of 3-substituted azetidines

248th National Meeting (2014)

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