Base-Induced Decarboxylation of Polyunsaturated α-Cyano Acids Derived from Malonic Acid: Synthesis of Sesquiterpene Nitriles and Aldehydes with β-, φ-, and ψ- End Groups

Abstract : Catalytic base-induced decarboxylation of polyunsaturated α-cyano-β-methyl acids derived from malonic acid led to the corresponding nitriles 3 (Schemes 2 and 3), 6 (Scheme 5), and 9 (Scheme 6). This decarboxylation occurred with previous deconjugation of the α,β-alkene moiety of the α-cyano-β-methyl acid, leading to an α-cyano-β-methylene propanoic acid which was easily decarboxylated (see Scheme 2). β-Methylene intermediates, in some cases, could be isolated; mechanistic pathways are proposed. The nitriles 3, 6, and 9 were reduced to the sesquiterpene aldehydes 4 (β-end group), 7 (φ-end group), and 10 (ψ-end group), respectively.
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Helvetica Chimica Acta, Wiley, 2013, 96 (2), pp.259--265. 〈10.1002/hlca.201200162〉
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http://hal.univ-reunion.fr/hal-01188108
Contributeur : Claire Tessier <>
Soumis le : vendredi 28 août 2015 - 15:06:11
Dernière modification le : vendredi 14 septembre 2018 - 08:14:30

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Laurent Dufossé, Dominique Cartier, Benoist Valla, Mireille Fouillaud, Roger Labia, et al.. Base-Induced Decarboxylation of Polyunsaturated α-Cyano Acids Derived from Malonic Acid: Synthesis of Sesquiterpene Nitriles and Aldehydes with β-, φ-, and ψ- End Groups. Helvetica Chimica Acta, Wiley, 2013, 96 (2), pp.259--265. 〈10.1002/hlca.201200162〉. 〈hal-01188108〉

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