Aminomethylation of Michael acceptors: complementary radical and polar approaches mediated by dialkylzincs.
Phtalimidomethyl iodide and substituted maleimidomethyl iodide were used as radical precursors in dialkylzinc-mediated radical addition to diethyl fumarate. The reactions led stereoselectively to functionalized pyrrolizidines. The radical mechanism was supported by spin-trapping experiments and rationalized by theoretical calculations. Radical additions, on the one hand, and carbozincation followed by transmetalation with copper(I), on the other, were shown to be complementary methods to achieve the formal aminomethylation of activated unsaturated compounds.
Institut de Chimie Radicalaire, UMR 7273, Faculté des Sciences et Techniques de Saint-Jérôme, Avenue Normandie-Niemen, Aix-Marseille Université, 13397 Marseille Cedex 20, France.
Julien
J
Maury
Dominique
D
Mouysset
Laurence
L
Feray
Sylvain R A
SR
Marque
Didier
D
Siri
Michèle P
MP
Bertrand