Asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes of glycine Schiff bases. Part 3: Michael addition reactions and miscellaneous transformations

• Published in: Amino acids Vol. 46; no. 9; pp. 2047 - 2073
• Main Authors: Aceña, José Luis, Sorochinsky, Alexander E., Soloshonok, Vadim
• Format: Journal Article
• Language: English
• Published: Vienna Springer Vienna 01-09-2014
• Subjects: Amino acids; Amino Acids - chemical synthesis; Amino Acids - chemistry; Analytical Chemistry; Asymmetry; Biochemical Engineering; Biochemistry; Biomedical and Life Sciences; Dealing; Glycine; Life Sciences; Matching; Michael reaction; Neurobiology; Nickel - chemistry; Proteomics; Review Article; Schiff bases; Synthesis; Transformations; Chiral auxiliary; Nickel; Asymmetric synthesis; Unnatural amino acids; Amino acids and peptides; Organometallic compounds
• ISSN: 0939-4451; 1438-2199
• DOI: 10.1007/s00726-014-1764-5

The major goal of this review is a critical discussion of the literature data on asymmetric synthesis of α-amino acids via Michael addition reactions involving Ni(II)-complexes of amino acids. The material covered is divided into two conceptually different groups dealing with applications of: (a) Ni(II)-complexes of glycine as
C
-nucleophiles and (b) Ni(II)-complexes of dehydroalanine as Michael acceptors. The first group is significantly larger and consequently subdivided into four chapters based on the source of stereocontrolling element. Thus, a chiral auxiliary can be used as a part of nucleophilic glycine Ni(II) complex, Michael acceptor or both, leading to the conditions of matching vs. mismatching stereochemical preferences. The particular focus of the review is made on the practical aspects of the methodology under discussion and mechanistic considerations.