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Asymmetric Access to α‐Substituted Functional Aspartic Acid Derivatives by a [3+2] Strategy Employing a Chiral Dienophile
Author(s) -
Ben Ayed Kawther,
Beauchard Anne,
Poisson JeanFrançois,
Py Sandrine,
Laurent Mathieu Y.,
Martel Arnaud,
Ammar Houcine,
Abid Souhir,
Dujardin Gilles
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301739
Subject(s) - enantiopure drug , chemistry , cleavage (geology) , aspartic acid , stereochemistry , side chain , enantioselective synthesis , organic chemistry , amino acid , catalysis , polymer , biochemistry , geotechnical engineering , fracture (geology) , engineering
Enantiopure vinyl ethers of Stericol ® 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.