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Synthesis of Benzonorcaradienes by Gold(I)-Catalyzed [4+3] Annulation

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posted on 15.11.2006, 00:00 by David J. Gorin, Pascal Dubé, F. Dean Toste
A formal [4 + 3]-annulation of vinyl arenes and diynyl propargyl esters is described. A mechanism involving cationic phosphinegold(I)-catalyzed tandem cyclopropanation/hydroarylation to produce the benzonorcaradiene products is proposed. In accord with this mechanism, the alkynyl cyclopropane can also be prepared with excellent regio- and diastereocontrol.