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A Cobalt‐Catalyzed Multicomponent Approach to Novel 2,3‐Di‐ and 2,2,3‐Trisubstituted 3‐Methoxycarbonyl‐γ‐butyrolactones
Author(s) -
Le Floch Camille,
Le Gall Erwan,
Léonel Eric,
Koubaa Jihen,
Martens Thierry,
Retailleau Pascal
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000698
Subject(s) - chemistry , cobalt , metalation , catalysis , domino , lactone , aryl , bromide , combinatorial chemistry , medicinal chemistry , organic chemistry , alkyl
A one‐pot, three‐component synthesis of the title butyrolactones starting from aryl bromides, dimethyl itaconate, and either aldehydes or ketones is described. The cobalt‐catalyzed domino process formally involves the in situ metalation of an aromatic bromide, conjugate addition onto dimethylitaconate, an aldolization reaction with a carbonyl compound and a final cyclization into a five‐membered lactone. This procedure is applied to the concise synthesis of a range of functionalized γ‐butyrolactones with a methyl paraconate subunit.