Synthesis of nitrogen-containing polycycles via rhodium (II)-induced cyclization-cycloaddition and insertion reactions of N-(diazoacetoacetyl) amides. Conformational …

…, RJ Pieters, J Taunton, HQ Pho, A Padwa…

Index: Doyle, Michael P.; Pieters, Roland J.; Taunton, Jack; Pho, Hoan Q.; Padwa, Albert; et al. Journal of Organic Chemistry, 1991 , vol. 56, # 18 p. 820 - 829

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Citation Number: 123

Abstract

A series of diazoacetoacetamides, when treated with a catalytic quantity of a rhodium (I1) carboxylate, were found to afford products derived from both a carbonyl ylide intermediate and intramolecular CH insertion. With 3-(N-(diazoacetoacetyl) amino) propanoate derivatives, the rhodium (II)-catalyzed carbenoid reactions exhibit a strong preference for formation of a@-lactam ring. This is attributed to a conformational preference that ...