A flexible, stereoselective dimethylzinc-mediated radical-anionic cascade: dramatic influence of additional Lewis acids.
Dimethylzinc-mediated addition of acyloxymethyl radicals to diethyl fumarate led to the highly stereoselective formation of disubstituted gamma-lactones in mean to good yields; this cascade provides a new example of a one-pot process mediated by dimethylzinc involving a tandem radical-anionic reaction; the chemoselectivity of the reaction was totally modified by additional Lewis acids.
Maury
Julien
J
Laboratoire Chimie Provence, UMR 6264, Equipe CMO, case 562, Université Aix-Marseille, FST Saint-Jérôme, av. Escadrille Normandie Niemen, 13397 Marseille cedex 20.
Feray
Laurence
L
Perfetti
Patricia
P
Bertrand
Michèle P
MP