Ti-mediated intramolecular cyclopropanation of N-alkenyl thioamides: scope and mechanistic study

Abstract : Although thioamides generally undergo a reductive alkylation process when they are treated with a Grignard reagent in the presence of Ti(OiPr)4, substrates fitted with a but-3-enyl substitution at the nitrogen atom are shown to be converted into bicyclic aminocyclopropanes. These reactions are compared with the similar cyclisations of the corresponding carboxylic amide substrates. A mechanistic study is provided. Coincidently, new reagent systems are identified for the mediation of the same transformation.
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Tetrahedron, Elsevier, 2014, 70 (25), pp.3924-3930. 〈10.1016/j.tet.2014.04.006〉
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Soumis le : jeudi 26 juin 2014 - 10:53:45
Dernière modification le : jeudi 10 mai 2018 - 02:07:51

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Fabien Hermant, Emmanuel Nicolas, Yvan Six. Ti-mediated intramolecular cyclopropanation of N-alkenyl thioamides: scope and mechanistic study. Tetrahedron, Elsevier, 2014, 70 (25), pp.3924-3930. 〈10.1016/j.tet.2014.04.006〉. 〈hal-01015278〉

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