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Pure Appl. Chem., 2011, Vol. 83, No. 3, pp. 621-631

Published online 2010-11-20

Multicomponent synthesis of polysubstituted γ‑butyrolactones under Barbier-like conditions

Camille Le Floch, Erwan Le Gall* and Eric Léonel

Equipe Électrochimie et Synthèse Organique, ESO, Institut de Chimie et des Matériaux Paris Est, ICMPE, UMR 7182 CNRS - Université Paris Est Créteil Val‑de-Marne, 2-8 rue Henri Dunant, 94320 Thiais, France

Abstract: The one-pot, three-component synthesis of 2,3-di- and 2,2,3-trisubstituted-3-methoxycarbonyl-γ-butyrolactones starting from aryl bromides, dimethyl itaconate, and aldehydes or ketones is described. The cobalt-catalyzed domino process formally involves the in situ metallation of an aromatic bromide, a conjugate addition onto dimethyl itaconate, an aldolization reaction with a carbonyl compound, and a final cyclization into a five-membered ring lactone. This procedure is applied to the concise synthesis of a range of polyfunctionalized γ-butyrolactones displaying a paraconic acid methyl ester subunit.