Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 18, Issue 11, Pages 3241-3247Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201102366
Keywords
aminomethylation; dialkylzincs; ESR experiments; radical reactions; theoretical calculations; zinc
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Funding
- ANR [D2R2, ANR-09-JCJC-0081]
- Agence Nationale de la Recherche (ANR) [ANR-09-JCJC-0081] Funding Source: Agence Nationale de la Recherche (ANR)
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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.
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