Domino Asymmetric Ring-Opening/Cross Metathesis Reaction

Significance

The first catalytic asymmetric ring-opening/cross-metathesis for enantioselective synthesis of nitrogen heterocycles is described. Functionalized piperidines are formed in excellent yields and selectivities. A large excess of styrene is added to minimize homodimerization, and electron-deficient styrenes provide lower ee values. As one of many post-modifications described by the authors, the products can be cleaved to a styrenyl olefin in high yield and diastereoselectivity.