Gold-catalyzed cycloisomerization of siloxy enynes to cyclohexadienes

Journal of the American Chemical Society
Liming Zhang, Sergey A Kozmin

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 degrees 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.

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Citations

Dec 1, 2011·Journal of the American Chemical Society·Hyun-Suk YeomSeunghoon Shin
Mar 30, 2012·Journal of the American Chemical Society·Yasunori MinamiTamejiro Hiyama
May 23, 2012·Journal of the American Chemical Society·Yunus E TürkmenViresh H Rawal
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Mar 9, 2011·Proceedings of the National Academy of Sciences of the United States of America·Jiayue CuiSergey A Kozmin
May 3, 2014·Chemical Communications : Chem Comm·Yongxiang LiuMaosheng Cheng
Jun 17, 2016·Angewandte Chemie·Minqiang Jia, Shengming Ma
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Dec 17, 2005·Chemistry : a European Journal·Cristina Nieto-OberhuberAntonio M Echavarren

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