Gold-catalyzed cycloisomerization of 1,5-allenynes via dual activation of an ene reaction |
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| Authors: | Cheong Paul Ha-Yeon Morganelli Philip Luzung Michael R Houk K N Toste F Dean |
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| Institution: | Department of Chemistry, University of California, Berkeley, California 94720, USA. |
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| Abstract: | Tris(triphenylphosphinegold) oxonium tetrafluoroborate, (Ph3PAu)3O]BF4, catalyzes the rearrangement of 1,5-allenynes to produce cross-conjugated trienes. Experimental and computational evidence shows that the ene reaction proceeds through a unique nucleophilic addition of an allene double bond to a cationic phosphinegold(I)-complexed phosphinegold(I) acetylide, followed by a 1,5-hydrogen shift. |
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