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Advanced asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid by alkylation/cyclization of newly designed axially chiral Ni(II) complex of glycine Schiff base

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Abstract

Asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid (vinyl-ACCA) is in extremely high demand due to the pharmaceutical importance of this tailor-made, sterically constrained α-amino acid. Here we report the development of an advanced procedure for preparation of the target amino acid via two-step SN2 and SN2′ alkylation of novel axially chiral nucleophilic glycine equivalent. Excellent yields and diastereoselectivity coupled with reliable and easy scalability render this method of immediate use for practical synthesis of (1R,2S)-vinyl-ACCA.

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Acknowledgments

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

Author information

Authors and Affiliations

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

    Aki Kawashima, Ryosuke Takeda, Akie Kawamura, Tatsunori Sato, Hiroki Moriwaki & Kunisuke Izawa

  2. Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai, 201203, China

    Shuangjie Shu, Jiang Wang & Hong Liu

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

    José Luis Aceña & Vadim A. Soloshonok

  4. IKERBASQUE, Basque Foundation for Science, Maria Diaz de Haro 3, 48013, Bilbao, Spain

    Vadim A. Soloshonok

Authors
  1. Aki Kawashima
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  2. Shuangjie Shu
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  3. Ryosuke Takeda
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  4. Akie Kawamura
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  5. Tatsunori Sato
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  6. Hiroki Moriwaki
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  7. Jiang Wang
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  8. Kunisuke Izawa
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  9. José Luis Aceña
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  10. Vadim A. Soloshonok
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  11. Hong Liu
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Corresponding author

Correspondence to Vadim A. Soloshonok.

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The authors declare that they have no conflict of interest.

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Handling Editor: P. Meffre.

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Kawashima, A., Shu, S., Takeda, R. et al. Advanced asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid by alkylation/cyclization of newly designed axially chiral Ni(II) complex of glycine Schiff base. Amino Acids 48, 973–986 (2016). https://doi.org/10.1007/s00726-015-2138-3

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  • DOI: https://doi.org/10.1007/s00726-015-2138-3

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