Aminomethylation of Michael Acceptors: Complementary Radical and Polar Approaches Mediated by Dialkylzincs

作者:Maury Julien; Mouysset Dominique; Feray Laurence*; Marque Sylvain R A; Siri Didier; Bertrand Michele P
来源:Chemistry - A European Journal, 2012, 18(11): 3241-3247.
DOI:10.1002/chem.201102366

摘要

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.

  • 出版日期2012-3