Enantioselective Cycloisomerization of 1,6-Enynes to Bicyclo[3.1.0]hexanes Catalyzed by Rhodium and Benzoic Acid

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• 作者：Koji Masutomi ; Keiichi Noguchi ; Ken Tanaka
• 刊名：Journal of the American Chemical Society
• 出版年：2014
• 出版时间：May 28, 2014
• 年：2014
• 卷：136
• 期：21
• 页码：7627-7630
• 全文大小：345K
• 年卷期：v.136,no.21(May 28, 2014)
• ISSN：1520-5126

文摘

It has been established that a cationic Rh(I)/(S)-Segphos or (S)-DTBM-Segphos complex and benzoic acid catalyze the enantioselective cycloisomerization of 1,6-enynes, possessing carbonyl groups at the enyne linkage, to 2-alkylidenebicyclo[3.1.0]hexanes. The present cycloisomerization may involve site selective 纬-hydrogen elimination. The one-pot enantioselective cycloisomerization and lactonization of 1,6-enynes, leading to bicyclic lactones, has also been accomplished.