Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5230695 | Tetrahedron | 2007 | 9 Pages |
Abstract
The sequence involving conjugate radical addition/aldol condensation/lactonization is a high yielding route to di- and tri-substituted γ-lactones starting from fumaric or maleic diesters. The reactions are mediated with dialkylzincs. The domino process relies on the ability of dialkylzinc to transform α-alkoxycarbonylalkyl radicals into zinc enolates. Compared to diethylzinc, dimethylzinc enables the use of a wider range of alkyl radical precursors. In addition, dimethylzinc is a convenient source of methyl radical, which leads to a straightforward synthesis of methylated derivatives related to α-methyl-paraconic acids.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Samantha Bazin, Laurence Feray, Nicolas Vanthuyne, Didier Siri, Michèle P. Bertrand,