Synthesis of benzonorcaradienes by gold(I)-catalyzed [4+3] annulation.
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.
Gorin
David J
DJ
Department of Chemistry, University of California, Berkeley, California 94720, USA.
Dubé
Pascal
P
Toste
F Dean
FD
D001555:Benzene Derivatives / Q000138:chemical synthesis*; D002384:Catalysis; D006046:Gold / Q000737:chemistry*
D001555:Benzene Derivatives; D006046:Gold