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

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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.

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Acknowledgments

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

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The authors declare that they have no conflict of interest.

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Authors and Affiliations

  1. Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, 20018, San Sebastián, Spain

    José Luis Aceña, Alexander E. Sorochinsky & Vadim Soloshonok

  2. IKERBASQUE, Basque Foundation for Science, 48011, Bilbao, Spain

    Alexander E. Sorochinsky & Vadim Soloshonok

  3. Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, Murmanska 1, Kyiv, 02660, Ukraine

    Alexander E. Sorochinsky

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  1. José Luis Aceña
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  2. Alexander E. Sorochinsky
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  3. Vadim Soloshonok
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Correspondence to José Luis Aceña or Vadim Soloshonok.

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Aceña, J.L., Sorochinsky, A.E. & Soloshonok, V. Asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes of glycine Schiff bases. Part 3: Michael addition reactions and miscellaneous transformations. Amino Acids 46, 2047–2073 (2014). https://doi.org/10.1007/s00726-014-1764-5

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