Journal
AMINO ACIDS
Volume 45, Issue 5, Pages 1017-1033Publisher
SPRINGER WIEN
DOI: 10.1007/s00726-013-1580-3
Keywords
Amino acids and peptides; Unnatural amino acids; Asymmetric synthesis; Chiral auxiliary; Organometallic compounds; Nickel
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Funding
- IKERBASQUE, Basque Foundation for Science
- Basque Government [SAIOTEK S-PE12UN044]
- Hamari Chemicals (Osaka, Japan)
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This review provides a comprehensive treatment of literature data dealing with asymmetric synthesis of alpha-amino-beta-hydroxy and alpha,beta-diamino acids via homologation of chiral Ni(II) complexes of glycine Schiff bases using aldol and Mannich-type reactions. These reactions proceed with synthetically useful chemical yields and thermodynamically controlled stereoselectivity and allow direct introduction of two stereogenic centers in a single operation with predictable stereochemical outcome. Furthermore, new application of Ni(II) complexes of alpha-amino acids Schiff bases for deracemization of racemic alpha-amino acids and (S) to (R) interconversion providing additional synthetic opportunities for preparation of enantiomerically pure alpha-amino acids, is also reviewed. Origin of observed diastereo-/enantioselectivity in the aldol, Mannich-type and deracemization reactions, generality and limitations of these methodologies are critically discussed.
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