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

β,γ-Unsaturated α-diazocarbonyl compounds possess two reactive sites for electrophilic addition – one at the diazo carbon and the other at the vinylogous γ-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 β,γ-unsaturated α-diazocarbonyl compounds and highlight the potential of this exciting research area and the many challenges that remain.

Graphical abstractβ,γ-Unsaturated α-diazocarbonyl compounds possess two reactive sites for electrophilic addition – one at the diazo carbon and the other at the vinylogous γ-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.Figure optionsDownload full-size imageDownload as PowerPoint slide