Asymmetric synthesis of alpha-amino acids via homologation of Ni(II) complexes of glycine Schiff bases. Part 2: Aldol, Mannich addition reactions, deracemization and (S) to (R) interconversion of alpha-amino acids

作者：Sorochinsky Alexander E^*; Luis Acena Jose; Moriwaki Hiroki; Sato Tatsunori; Soloshonok Vadim

来源：Amino Acids, 2013, 45(5): 1017-1033.

DOI：10.1007/s00726-013-1580-3

• Amino acids and peptides
• Unnatural amino acids
• Asymmetric synthesis
• Chiral auxiliary
• Organometallic compounds
• Nickel

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.

• 出版日期2013-11