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Gold-Catalyzed Formation of Oxonium Ions from Enynes and Their Intra- and Intermolecular Trapping with Allylsilanes

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journal contribution
posted on 06.01.2012, 00:00 by Jingwei Li, Xiaoguang Liu, Daesung Lee
Gold-catalyzed ring closure of 1,5-enyne containing a silyl ether at the allylic position induces a skeletal rearrangement to form an oxonium intermediate, which then undergoes a smooth allylation in both an intra- and intermolecular manner. In the intramolecular allyl transfer, the additive alcohol becomes positioned on the silicon of the silyl ether by forming a new Si–OR bond, whereas, in the intermolecular allylation, the alcohol is incorporated in the homoallylic carbon by forming a C–OR bond.