Gold(I)-Catalyzed Formation of Bicyclo[4.2.0]oct-1-enes

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• 作者：Ryan J. Felix ; Osvaldo Gutierrez ; Dean J. Tantillo ; Michel R. Gagn茅
• 刊名：The Journal of Organic Chemistry
• 出版年：2013
• 出版时间：June 7, 2013
• 年：2013
• 卷：78
• 期：11
• 页码：5685-5690
• 全文大小：327K
• 年卷期：v.78,no.11(June 7, 2013)
• ISSN：1520-6904

文摘

Gold(I) catalysts effectively promote the Cope rearrangement of acyclic 1,5-dienes bearing a terminal cyclopropylidene. When this methodology is applied to cyclic substrates an unexpected transformation occurs, resulting in the formation of a tricyclic compound incorporating a bicyclo[4.2.0]oct-1-ene core, a portion of which is found in a number of natural products. Density functional theory calculations (M06 and M06-2X) reveal insight into the mechanism and thermodynamics of this unique transformation.