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 al...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2006-11, Vol.128 (45), p.14480-14481
Main Authors: Gorin, David J, Dubé, Pascal, Toste, F. Dean
Format: Article
Language:English
Subjects:
Benzene Derivatives - chemical synthesis
Catalysis
Chemistry
Exact sciences and technology
General and physical chemistry
Gold - chemistry
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja066694e