A new method for the synthesis of cyclopentenones via the tandem Michael addition-carbene insertion reaction of. beta.-ketoethynyl (phenyl) iodonium salts

BL Williamson, RR Tykwinski…

Index: Williamson, Bobby L.; Tykwinski, Rik R.; Stang, Peter J. Journal of the American Chemical Society, 1994 , vol. 116, # 1 p. 93 - 98

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Citation Number: 66

Abstract

Abstract: A variety of substituted 2-cyclopentenones are obtained in good yields (5342%) via intramolecular 1, 5-carbon-hydrogen insertion reactions of [b-(p-toluenesulfonyl) alkylidene] carbenes derived from Michael addition of sodium p-toluenesulfinate to fl-ketoethynyl (phenyl) iodonium triflates. An extension of the methodology using 8-amidoethynyl (pheny1) iodonium triflates provides a facile synthesis of y-lactams including fused bicyclic systems. ...