Gold-Catalyzed Cycloisomerization of 1,5-Allenynes via Dual Activation of an Ene Reaction

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• 作者：Paul Ha-Yeon Cheong ; Philip Morganelli ; Michael R. Luzung ; K. N. Houk ; F. Dean Toste
• 刊名：Journal of the American Chemical Society
• 出版年：2008
• 出版时间：April 2, 2008
• 年：2008
• 卷：130
• 期：13
• 页码：4517 - 4526
• 全文大小：678K
• 年卷期：v.130,no.13(April 2, 2008)
• ISSN：1520-5126

文摘

Tris(triphenylphosphinegold) oxonium tetrafluoroborate, [(Ph₃PAu)₃O]BF₄, catalyzes the rearrangement of 1,5-allenynes to produce cross-conjugated trienes. Experimental and computational evidenceshows that the ene reaction proceeds through a unique nucleophilic addition of an allene double bond toa cationic phosphinegold(I)-complexed phosphinegold(I) acetylide, followed by a 1,5-hydrogen shift.