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Aminomethylation of Michael Acceptors: Complementary Radical and Polar Approaches Mediated by Dialkylzincs
Author(s) -
Maury Julien,
Mouysset Dominique,
Feray Laurence,
Marque Sylvain R. A.,
Siri Didier,
Bertrand Michèle P.
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201102366
Subject(s) - transmetalation , iodide , chemistry , polar , iodine , copper , organic chemistry , medicinal chemistry , photochemistry , catalysis , physics , astronomy
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.