Divergent pathways of β,γ-unsaturated α-diazocarbonyl compounds catalyzed by dirhodium and Lewis acids catalysts separately or in combination

beta,gamma-Unsaturated alpha-diazocarbonyl compounds possess two reactive sites for electrophilic addition - one at the diazo carbon and the other at the vinylogous gamma-position. Controlled by catalyst, divergent transformations are achieved starting from the same starting materials, either by Lewis acid-catalyzed addition or by dirhodium-catalyzed metal carbene reactions. In select cases two catalysts working in combination or in sequence provide a relay for cascade transformations. In this review, we summarize advances in catalyst-dependent divergent transformations of beta,gamma-unsaturated alpha-diazocarbonyl compounds and highlight the potential of this exciting research area and the many challenges that remain. (C) 2014 Xin-Fang Xu. Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. All rights reserved.