Tandem cyclization-cycloaddition reaction of rhodium carbenoids. Scope and mechanistic details of the process

A Padwa, GE Fryxell, L Zhi

Index: Padwa; Fryxell; Zhi Journal of the American Chemical Society, 1990 , vol. 112, # 8 p. 3100 - 3109

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Citation Number: 150

Abstract

Abstract: Treatment of I-diazo-2, s-pentanediones with rhodium (I1) carboxylates affords cyclic six-ring carbonyl ylide dipoles. These species undergo facile 1, 3-dipolar cycloaddition with both electron-deficient and electron-rich dipolarophiles. In certain cases 2: l cycloadducts are formed. The higher order cycloadducts are derived by further dipolar cycloaddition of the carbonyl ylide across the keto group of the initially formed 1: l ...