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Recent approaches for asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes

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Abstract

This review article critically discusses examples of asymmetric synthesis of tailor-made α-amino acids via homologation of Ni(II) complexes of glycine and alanine Schiff bases, reported in the literature from 2013 through the end of 2016. Where it is possible, reaction mechanism and origin of the stereochemical outcome is discussed in detail. Special attention is given to various aspects of practicality and scalability of the reported methods. Among the most noticeable developments in this area are novel designs of axially chiral ligands, application of electro- and mechano-chemical (ball-milling) conditions, and development of dynamic kinetic resolution procedures.

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Acknowledgements

The authors gratefully acknowledge financial support from Ikerbasque, Basque Foundation for Science, National Natural Science Foundation of China (81620108027 and 21632008), the Major Project of Chinese National Programs for Fundamental Research and Development (2015CB910304).

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Authors and Affiliations

  1. State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai, 201203, China

    Yibing Wang, Xiaohan Song, Jiang Wang & Hong Liu

  2. University of Chinese Academy of Sciences, No. 19A Yuquan Road, Beijing, 100049, China

    Yibing Wang, Xiaohan Song, Jiang Wang & Hong Liu

  3. Hamari Chemicals Ltd., 1-4-29 Kunijima, Higashi-Yodogawa-ku, Osaka, 533-0024, Japan

    Hiroki Moriwaki

  4. Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, Paseo Manuel Lardizábal 3, 20018, San Sebastián, Spain

    Vadim A. Soloshonok

  5. Ikerbasque, Basque Foundation for Science, Maria Diaz de Haro 3, 48013, Bilbao, Spain

    Vadim A. Soloshonok

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  1. Yibing Wang
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  2. Xiaohan Song
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  3. Jiang Wang
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  4. Hiroki Moriwaki
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  5. Vadim A. Soloshonok
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Wang, Y., Song, X., Wang, J. et al. Recent approaches for asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes. Amino Acids 49, 1487–1520 (2017). https://doi.org/10.1007/s00726-017-2458-6

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