Abstract
The efficient gold-catalyzed cyclization reactions of alkynyl silyl enol ethers were successfully applied to the preparation of bicyclo[3.2.1]octanone derivatives. Accordingly, after optimization of the gold catalytic system, several bicyclic α,β-unsaturated keto adducts were synthesized in good to excellent yields. The process followed a major 5-exo cyclization via an anti addition of the silyl enol ether to the π-activated intermediate, which was demonstrated by a deuterium incorporation experiment. A 6-endo cyclization process was observed for a silyl enol ether bearing an electron-donating aromatic group.
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