Brønsted Acid Catalyzed Highly Diastereoselective Michael-Type Addition of Azlactones to Enones

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Abstract

A highly regio- and diastereoselective 1,4-addition of azlactones to enones catalyzed by a Brønsted acid is described. The Michael adducts were prepared in moderate to good yields and with complete control of the relative stereochemistry. In addition, two consecutive stereogenic centers were created, one of which was a quaternary stereocenter. The method was successfully extended to the first highly diastereoselective desymmetrization of dibenzylidene acetone.

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