Abstract
A variety of substituted 2-cyclopentenones are obtained in good yields (53-82%) via intramolecular 1,5-carbon-hydrogen insertion reactions of [β-(p-toluenesulfonyl)alkylidene]carbenes derived from Michael addition of sodium p-toluenesullanate to β-ketoethynyl(phenyl)iodonium triflates. An extension of the methodology using β-amidoethynyl(phenyl)iodonium triflates provides a facile synthesis of γ-lactams including fused bicyclic systems. The isomerization of a substituted cyclopentenone on silica gel is also reported
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