Title: Stereochemically defined C-substituted glutamic acids and their derivatives. 1. An efficient asymmetric synthesis of (2S,3S)-3-methyl- and -3-trifluoromethylpyroglutamic acids
Authors: Soloshonok, VA ×
Cai, CZ
Hruby, VJ
Van Meervelt, Luc
Mischenko, N #
Issue Date: Jan-1999
Publisher: Pergamon-elsevier science ltd
Series Title: Tetrahedron vol:55 issue:41 pages:12031-12044
Abstract: An efficient asymmetric synthesis of biologically important (2S,3S)-3-methyl- and (2S,3S)-3-trifluoromethylpyroglutamic acid has been developed. We method consists of diastereoselective Michael addition reaction between ethyl crotonate or ethyl 4,4,4-trifluorocrotonate and a Ni(II) complex of the chiral non-racemic Schiff base of glycine with (S)-o-[N-(N-benzylprolyl)amino]benzophenone (BPB) followed by decomposition of the addition products by aq. HCl and treatment of the resultant glutamic acid derivatives with NH4OH to afford the target pyroglutamic acids along with recovery of the chiral auxiliary BPB. The stereochemical outcome of the addition reactions was found to be subjected to kinetic control. A mechanistic rationale for the observed stereochemical preferences is discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.
ISSN: 0040-4020
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Biochemistry, Molecular and Structural Biology Section
× corresponding author
# (joint) last author

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