The Journal of Organic Chemistry

A Novel Cycloaddition Reaction of α-Diazo-γ-amido Ketones Catalyzed by Rhodium (II) Acetate. Scope and Mechanistic Details of the Process

A Padwa, AT Price, L Zhi

Index: Pawda, Albert; Price, Alan T.; Zhi, Lin Journal of Organic Chemistry, 1996 , vol. 61, # 7 p. 2283 - 2292

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Citation Number: 21

Abstract

α-Diazo ketones containing an amido group in the γ-position have been found to undergo a novel rhodium (II)-catalyzed cycloaddition reaction. Intramolecular cyclization of the keto carbenoid onto the oxygen atom of the amide group generates a carbonyl ylide dipole as a