A Flexible, Stereoselective Dimethylzinc-Mediated Radical-Anionic Cascade: Dramatic Influence of Additional Lewis Acids

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 γ-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;...

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Veröffentlicht in:Organic letters 2010-08, Vol.12 (16), p.3590-3593
Hauptverfasser: Maury, Julien, Feray, Laurence, Perfetti, Patricia, Bertrand, Michèle P
Format: Artikel
Sprache:eng
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Chemical Sciences
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Zusammenfassung:Dimethylzinc-mediated addition of acyloxymethyl radicals to diethyl fumarate led to the highly stereoselective formation of disubstituted γ-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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol101519w