150. Metal Carbene-Promoted Sequential Transformations for the Enantioselective Synthesis of Highly Functionalized Cycloheptadienes

Authors: Liang Deng , Anthony J. Giessert , Oksana O. Gerlitz , Xing Dai , Steven T. Diver and Huw M. L. Davies

J. Am. Chem. Soc.,

2005, 127 (5), 1342–1343


A two-step, three-component coupling of an alkyne, enol ether, and vinyl diazoester was accomplished by use of successive metal carbene-catalyzed transformations. This efficient approach to cycloheptadienes is both diastereo- and enantioselective. Kinetic resolution was accomplished on dienol ethers bearing a racemic chiral center at the propargylic position. A model is offered which explains the observed selectivity and accounts for the reactivity difference between trans- and cis-dienol ethers.

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