Asymmetric Synthesis of 4,4-(Difluoro)glutamic Acid via Chiral Ni(II)-Complexes of Dehydroalanine Schiff Bases. Effect of the Chiral Ligands Structure on the Stereochemical Outcome.

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ID: 91070
2020
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Abstract
Four differently substituted chiral Ni(II)-complexes of dehydroalanine Schiff base were prepared and reacted with BrCFCOOEt/Cu under the standard reaction conditions. The observed diastereoselectivity was found to depend on the degree and pattern of chlorine substitution for hydrogen in the structure of the dehydroalanine complexes. The unsubstituted complex gave the ratio of diastereomers ()(2)/()(2) of 66/34. On the other hand, introduction of chlorine atoms in the strategic positions on the chiral ligands allowed to achieve a practically attractive diastereoselectivity of (∼98.5/1.5). Diastereomerically pure major product was disassembled to prepare 9-fluorenylmethyloxycarbonyl (Fmoc) derivative of ()-4,4-difluoroglutamic acid.
Reference Key
tokairin2020asymmetricchemistryopen Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Tokairin, Yoshinori;Shigeno, Yuhei;Han, Jianlin;Röschenthaler, Gerd-Volker;Konno, Hiroyuki;Moriwaki, Hiroki;Soloshonok, Vadim A;
Journal chemistryopen
Year 2020
DOI
10.1002/open.201900343
URL
Keywords
asymmetric synthesis fluorine ni(ii)-complexes schiff bases tailor-made amino acids

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