Asymmetric addition of a nitrogen nucleophile to an enoate in the presence of a chiral phase-transfer catalyst: A novel approach toward enantiomerically enriched protected beta-amino acids

Markus Weiss; Sonja Borchert; Emmanuelle Remond; Sylvain Juge; Harald Groeger

doi:10.1002/hc.21004

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Asymmetric addition of a nitrogen nucleophile to an enoate in the presence of a chiral phase-transfer catalyst: A novel approach toward enantiomerically enriched protected beta-amino acids

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Asymmetric addition of a nitrogen nucleophile to an enoate in the presence of a chiral phase-transfer catalyst: A novel approach toward enantiomerically enriched protected beta-amino acids

Markus Weiss, Sonja Borchert, Emmanuelle Remond, Sylvain Juge et Harald Groeger

Heteroatom chemistry, Vol.23(2), pp.202-209

01/01/2012

DOI: https://doi.org/10.1002/hc.21004

Résumé

Chemistry

Chemistry, Multidisciplinary

Physical Sciences

Science & Technology

A proof of concept for the asymmetric organocatalytic aza-Michael addition reaction of nitrogen nucleophiles with simple and readily available alkyl enoates as acceptor molecules in the presence of a chiral phase-transfer catalyst has been demonstrated. The desired enantiomerically enriched beta-amino acid derivatives were obtained in up to 86% yield and with enantioselectivities of up to 37% ee. (C) 2012 Wiley Periodicals, Inc. Heteroatom Chem 23:202209, 2012; View this article online at . DOI 10.1002/hc.21004

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Détails

Titre: Asymmetric addition of a nitrogen nucleophile to an enoate in the presence of a chiral phase-transfer catalyst: A novel approach toward enantiomerically enriched protected beta-amino acids
Créateurs - sans rôle: Markus Weiss - Univ Erlangen Nurnberg, Dept Chem & Pharm, D-91054 Erlangen, Germany
Sonja Borchert - Univ Erlangen Nurnberg, Dept Chem & Pharm, D-91054 Erlangen, Germany
Emmanuelle Remond - Univ Bourgogne, Inst Chim Mol, UMR CNRS 5260, F-21078 Dijon, France
Sylvain Juge - Univ Bourgogne, Inst Chim Mol, UMR CNRS 5260, F-21078 Dijon, France
Harald Groeger - Univ Erlangen Nurnberg, Dept Chem & Pharm, D-91054 Erlangen, Germany
Détails de publication: Heteroatom chemistry, Vol.23(2), pp.202-209
Éditeur: Wiley-Hindawi
Nombre de pages: 8
Note de subvention: Deutsche Bundesstiftung Umwelt
Identifiants: 99138893009311
Unité académique: Institut des Biomolécules Max Mousseron - IBMM
Langue: English
Type de ressource: Journal article