Gold-Catalyzed Cycloisomerization of Siloxy Enynes to Cyclohexadienes
- 1 September 2004
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (38) , 11806-11807
- https://doi.org/10.1021/ja046112y
Abstract
We have described the first Au-catalyzed cycloisomerization of 1-siloxy-5-en-1-ynes. The reaction is efficiently catalyzed by AuCl (1 mol %) to afford siloxy cyclohexadienes, which can be readily converted to the corresponding 1,2- and 1,3-cyclohexenones. The catalytic process displays a broad substrate scope and exceedingly mild reaction conditions (30 min, 20 °C). The presence of a siloxy alkyne moiety is crucial for enabling the skeletal reorganization process, which is postulated to proceed via a novel reaction mechanism involving a cascade of 1,2-alkyl migrations.Keywords
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