Tetrahedron Asymmetry p. 3545 - 3551 (1996)
Update date:2022-08-02
Topics:
Kokuryo, Yoshitsugu
Nakatani, Takuji
Kobayashi, Kobee
Tamura, Yoshinori
Kawada, Kenji
Ohtani, Mitsuaki
Enantiomerically pure L-erythro- and L-threo-4-fluoroglutamic acids 1a and 1b were conveniently prepared. The key steps in this synthesis relied upon separation of diastereomers of N-chloroacetyl-4-fluoroglutamic acid 5-methyl ester 7 by recrystallization and enzymatic resolution of enantiomers of the resulting 7(a+c) and 7(b+d) by aminoacylase. Protection of the γ-carboxyl group as a methyl ester was found to be crucial for this enzymatic reaction.
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