Regioncontrol by the carbon-carbon double bond in the Rh2(OAc)4 mediated carbon-hydrogen insertion of α-diazo-ketones

Article abstract of DOI:10.1016/S0040-4020(01)89741-6

Diazo carbonyl compounds, when catalyzed by dirhodium tetraacetate, insert to allylic position. This phenomenon was exploited in cyclic systems 3d, 5d, 5g, and 10. The reactivity toward allylic insertion is corroborated by the unexpected six-membered ring cyclization in the transforming 5g→9.