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Amino Acids

, Volume 46, Issue 9, pp 2047–2073 | Cite as

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

  • José Luis AceñaEmail author
  • Alexander E. Sorochinsky
  • Vadim SoloshonokEmail author
Review Article

Abstract

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.

Keywords

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

Notes

Acknowledgments

We thank IKERBASQUE, Basque Foundation for Science; the Basque Government (SAIOTEK S-PE13UN098) and Hamari Chemicals (Osaka, Japan) for generous financial support.

Conflict of interest

The authors declare that they have no conflict of interest.

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© Springer-Verlag Wien 2014

Authors and Affiliations

  1. 1.Department of Organic Chemistry I, Faculty of ChemistryUniversity of the Basque Country UPV/EHUSan SebastiánSpain
  2. 2.IKERBASQUE, Basque Foundation for ScienceBilbaoSpain
  3. 3.Institute of Bioorganic Chemistry and PetrochemistryNational Academy of Sciences of UkraineKyivUkraine

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