1.
Angew Chem Int Ed Engl
; 57(21): 6284-6288, 2018 05 22.
Artículo
en Inglés
| MEDLINE
| ID: mdl-29645401
RESUMEN
We report a phosphine-catalyzed activation of electron-deficient vinylcyclopropanes (VCPs) to generate an ambident C5 synthon that is poised to undergo consecutive reactions. The utility of the activation is demonstrated in a phosphine-catalyzed rearrangement of vinylcyclopropylketones to cycloheptenones in good yields with a broad substrate scope. Mechanistic investigations support a stepwise process comprising homoconjugate addition, water-assisted proton transfer, and 7-endo-trig SN 2' ring closure.