Asymmetric synthesis of enantiomerically and diastereoisomerically enriched 4-[F or Br]-substituted glutamic acids

被引：0
作者：
Yuri N. Belokon
Victor I. Maleev
Tatiana F. Savel’eva
Margarita A. Moskalenko
Dmitri A. Pripadchev
Victor N. Khrustalev
Ashot S. Saghiyan
机构：
[1] A. N. Nesmeyanov Institute of Organoelement Compounds Russian Academy of Science,Chemistry Department, Chair of Pharmaceutical Chemistry
[2] Yerevan State University,undefined
来源：
Amino Acids | 2010年 / 39卷
关键词：
Asymmetric synthesis; Chiral Ni; Schiff base complexes; (2; )-4-[; F or ; F]fluoroglutamic acid; (1; ,2; )-1-aminocyclopropane-1,2-dicarboxylic acid; (1; ,2; )-1-aminocyclopropane-1,2-dicarboxylic acid; (2; ,4; )-4-bromoglutamic acid;
D O I：
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中图分类号：
学科分类号：
摘要：
A novel simple synthetic protocol for the preparation of both (2S,4R)- and (2S,4S)-FGlu, applying Michael addition of methyl α-fluoroacrylate to a NiII complex of glycine Schiff base with BPB, was elaborated. In addition, same reaction of mentioned complex with ethyl α-bromoacrylate leads to the NiII complex of the Schiff base of BPB with (2S,4R)-4-bromo-glutamic acid monoester, that can be transformed into the corresponding complexes of 1-aminocyclopropane-1,2-dicarboxylic acid. The decomposition of the diastereoisomerically pure complexes leads to corresponding enantiomerically enriched (ee > 98%) amino acids.
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页码：1171 / 1176
页数：5
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