A useful α, α′-annulation reaction of enamines

AJ Frontier, SJ Danishefsky, GA Koppel, D Meng

Index: Frontier, Alison J.; Danishefsky, Samuel J.; Koppel, Gary A.; Meng, Dongfang Tetrahedron, 1998 , vol. 54, # 42 p. 12721 - 12736

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Citation Number: 24

Abstract

The reactions of a series of enamines generated from a range of cyclic ketones with chloromethyl and iodomethyl vinyl ketone have been studied. The principal products are bridged ring diketones. The four carbon bridge, bearing a 2-oxobutyl function, spans the α and α′ carbons of the original cyclanone. Presumptive evidence as to the pathway of this novel one step bridging annulation is provided.