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Unexpected Cycloisomerizations of Nonclassical Carbocation Intermediates in Gold(I)-Catalyzed Homo-Rautenstrauch Cyclizations

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journal contribution
posted on 15.07.2011, 00:00 by Guan Wang, Yue Zou, Zhiming Li, Quanrui Wang, Andreas Goeke
An unexpected gold(I)-catalyzed homo-Rautenstrauch rearrangement of 1-cyclopropyl propargylic esters to cyclohexenones is disclosed. This rearrangement represents new evidence for the recently discussed gold-stabilized nonclassical carbocation character of intermediates in gold catalysis. A mechanistic study proved partial chirality transfer from optically active propargyl acetates.