SN2 vs. E2 on quaternary centres: an application to the synthesis of enantiopure β2,2-amino acids

Alberto Avenoza; Jesús H. Busto; Francisco Corzana; Gonzalo Jiménez-Osés; Jesús M. Peregrina

doi:10.1039/B400282B

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S_N2 vs. E2 on quaternary centres: an application to the synthesis of enantiopure β^2,2-amino acids†

Alberto Avenoza,*^a Jesús H. Busto,^a Francisco Corzana,^a Gonzalo Jiménez-Osés^a and Jesús M. Peregrina*^a

Author affiliations

* Corresponding authors

^a Departamento de Química, Universidad de La Rioja, Grupo de Síntesis Química de La Rioja, U.A.-C.S.I.C., Logroño, Spain
E-mail: alberto.avenoza@dq.unirioja.es
Fax: +34 941 299655
Tel: +34 941 299655

Abstract

S_N2 and E2 competing reactions in cyclic sulfamidates can be modulated by the change of an amide group to an ester group attached to the quaternary carbon activated for the nucleophilic attack, allowing an easy approach to enantiopure α,α-disubstituted β-amino acids.

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Article information

DOI: https://doi.org/10.1039/B400282B
Article type: Communication
Submitted: 09 Jan 2004
Accepted: 25 Feb 2004
First published: 16 Mar 2004

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Chem. Commun., 2004, 980-981

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S_N2 vs. E2 on quaternary centres: an application to the synthesis of enantiopure β^2,2-amino acids

A. Avenoza, J. H. Busto, F. Corzana, G. Jiménez-Osés and J. M. Peregrina, Chem. Commun., 2004, 980 DOI: 10.1039/B400282B

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