Document Detail


Asymmetric synthesis of enantiomerically and diastereoisomerically enriched 4-[F or Br]-substituted glutamic acids.
MedLine Citation:
PMID:  20306095     Owner:  NLM     Status:  In-Process    
Abstract/OtherAbstract:
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.
Authors:
Yuri N Belokon; Victor I Maleev; Tatiana F Savel'eva; Margarita A Moskalenko; Dmitri A Pripadchev; Victor N Khrustalev; Ashot S Saghiyan
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2010-03-20
Journal Detail:
Title:  Amino acids     Volume:  39     ISSN:  1438-2199     ISO Abbreviation:  Amino Acids     Publication Date:  2010 Nov 
Date Detail:
Created Date:  2010-10-26     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9200312     Medline TA:  Amino Acids     Country:  Austria    
Other Details:
Languages:  eng     Pagination:  1171-6     Citation Subset:  IM    
Affiliation:
A. N. Nesmeyanov Institute of Organoelement Compounds Russian Academy of Science, B-334, Vavilova str. 28, Moscow, 119991, Russia. yubel@ineos.ac.ru
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