Radical addition of nitrones to acrylates mediated by SmI2: asymmetric synthesis of γ-amino acids employing carbohydrate-based chiral auxiliaries

Sine A. Johannesen; Silvia Albu; Rita G. Hazell; Troels Skrydstrup

doi:10.1039/B405141F

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Radical addition of nitrones to acrylates mediated by SmI₂: asymmetric synthesis of γ-amino acids employing carbohydrate-based chiral auxiliaries†

Sine A. Johannesen,^a Silvia Albu,^a Rita G. Hazell^a and Troels Skrydstrup*^a

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* Corresponding authors

^a Department of Chemistry, University of Aarhus, Langelandsgade 140, 8000 Aarhus C, Denmark
E-mail: ts@chem.au.dk
Fax: +45 8619 6199
Tel: +45 8942 3932

Abstract

Alkyl nitrones possessing N-substituted sugars as chiral auxiliaries were found to effectively undergo an SmI₂-mediated radical addition to n-butyl acrylate affording γ-amino acid derivatives with high diastereomeric control.

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Article information

DOI: https://doi.org/10.1039/B405141F
Article type: Communication
Submitted: 07 Apr 2004
Accepted: 03 Jun 2004
First published: 19 Jul 2004

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Chem. Commun., 2004, 1962-1963

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Radical addition of nitrones to acrylates mediated by SmI₂: asymmetric synthesis of γ-amino acids employing carbohydrate-based chiral auxiliaries

S. A. Johannesen, S. Albu, R. G. Hazell and T. Skrydstrup, Chem. Commun., 2004, 1962 DOI: 10.1039/B405141F

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