Title: An efficient asymmetric synthesis of (2S,3S)-3-trifluoromethylpyroglutamic acid
Authors: Soloshonok, VA ×
Avilov, DV
Kukhar, VP
Van Meervelt, Luc
Mischenko, N #
Issue Date: Jan-1997
Publisher: Pergamon-elsevier science ltd
Series Title: Tetrahedron letters vol:38 issue:27 pages:4903-4904
Abstract: The stereochemical outcome of the Michael reaction between ethyl 4,4,4-trifluorocrotonate and a Ni(ID complex of the Schiff base of glycine with (S)-o-[N-(N-benzylprolyl)amino]benzophenone was found to be subjected to kinetic and thermodynamic control. Thus, under kinetically controlled conditions high values of diastereo-selectivity, up to 94% de, allowing for an efficient asymmetric synthesis of (2S,3S)-3-trifluoromethylpyroglutamic acid, could be obtained, while the thermodynamically controlled stereoselectivity is rather modest (54-60% de). (C) 1997 Elsevier Science Ltd.
ISSN: 0040-4039
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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