Asymmetric Access to alpha-Substituted Functional Aspartic Acid Derivatives by a [3+2] Strategy Employing a Chiral Dienophile

Kawther Ben Ayed; Anne Beauchard; Jean-Francois Poisson; Sandrine Py; Mathieu Y. Laurent; Arnaud Martel; Houcine Ammar; Souhir Abid; Gilles Dujardin

doi:10.1002/ejoc.201301739

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Asymmetric Access to alpha-Substituted Functional Aspartic Acid Derivatives by a [3+2] Strategy Employing a Chiral Dienophile

Journal article

Peer reviewed

Asymmetric Access to alpha-Substituted Functional Aspartic Acid Derivatives by a [3+2] Strategy Employing a Chiral Dienophile

Kawther Ben Ayed, Anne Beauchard, Jean-Francois Poisson, Sandrine Py, Mathieu Y. Laurent, Arnaud Martel, Houcine Ammar, Souhir Abid and Gilles Dujardin

European journal of organic chemistry, Vol.2014(14), pp.2924-2932

05/2014

DOI: https://doi.org/10.1002/ejoc.201301739

Abstract

Chemistry

Chemistry, Organic

Physical Sciences

Science & Technology

Enantiopure vinyl ethers of Stericol((R)) underwent diastereoselective thermal 1,3 dipolar cycloadditions with N-benzyl, N-benzhydryl, and N-PMB aspartate ester nitrones. Chemoselective N-debenzylation of the resulting cycloadducts afforded diastereomerically and enantiomerically pure crystalline NH-isoxazolidine, the absolute configuration of which was established by X-ray crystallography. N-Protection and N-O cleavage of this isoxazolidine gave enantioenriched quaternary aspartate derivatives bearing functionalized side chains.

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Title: Asymmetric Access to alpha-Substituted Functional Aspartic Acid Derivatives by a [3+2] Strategy Employing a Chiral Dienophile
Creators - without role: Kawther Ben Ayed - Institut des Molécules et Matériaux du Mans
Anne Beauchard - Institut des Molécules et Matériaux du Mans
Jean-Francois Poisson - Département de Chimie Moléculaire
Sandrine Py - Département de Chimie Moléculaire
Mathieu Y. Laurent - Institut des Molécules et Matériaux du Mans
Arnaud Martel - Institut des Molécules et Matériaux du Mans
Houcine Ammar - University of Sfax
Souhir Abid - University of Sfax
Gilles Dujardin - Institut des Molécules et Matériaux du Mans
Publication Details: European journal of organic chemistry, Vol.2014(14), pp.2924-2932
Publisher: Wiley
Number of pages: 9
Grant note: University of Sfax BS07-005-01 / Agence Nationale de la Recherche (ANR); French National Research Agency (ANR)
Identifiers: 9912798308331
Academic Unit: Al Jouf University
Language: English
Resource Type: Journal article