Asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid by sequential SN2–SN2′ dialkylation of (R)-N-(benzyl)proline-derived glycine Schiff base Ni(II) complex

Aki Kawashima; Chen Xie; Haibo Mei; Ryosuke Takeda; Akie Kawamura; Tatsunori Sato; Hiroki Moriwaki; Kunisuke Izawa; Jianlin Han; José Luis Aceña; Vadim A. Soloshonok

doi:10.1039/C4RA12658K

Asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid by sequential S_N2–S_N2′ dialkylation of (R)-N-(benzyl)proline-derived glycine Schiff base Ni(ii) complex†

Aki Kawashima,^a Chen Xie,^b Haibo Mei,^b Ryosuke Takeda,^a Akie Kawamura,^a Tatsunori Sato,^a Hiroki Moriwaki,^a Kunisuke Izawa,^a Jianlin Han,*^b José Luis Aceña*^c and Vadim A. Soloshonok*^cd

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* Corresponding authors

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

^b School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, China
E-mail: hanjl@nju.edu.cn
Fax: +86-25-83686133
Tel: +86-25-83686133

^c Department of Organic Chemistry I, Faculty of Chemistry, University of The Basque Country UPV/EHU, 20018 San Sebastián, Spain
E-mail: vadym.soloshonok@ehu.es
Fax: +34-943-015270
Tel: +34-943-015177

^d IKERBASQUE, Basque Foundation for Science, María Díaz de Haro 3, 48013 Bilbao, Spain

Abstract

This work describes a new process for the asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid of high pharmaceutical importance. The sequence of the reactions includes PTC alkylation (S_N2), homogeneous S_N2′ cyclization followed by disassembly of the resultant Ni(II) complex. All reactions are conducted under operationally convenient conditions and suitably scaled up to 6 g of the starting Ni(II) complex.

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Asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid by sequential S_N2–S_N2′ dialkylation of (R)-N-(benzyl)proline-derived glycine Schiff base Ni(ii) complex†

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Asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid by sequential S_N2–S_N2′ dialkylation of (R)-N-(benzyl)proline-derived glycine Schiff base Ni(II) complex

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RSC Advances

Asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid by sequential SN2–SN2′ dialkylation of (R)-N-(benzyl)proline-derived glycine Schiff base Ni(ii) complex†

Abstract

Supplementary files

Article information

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Asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid by sequential SN2–SN2′ dialkylation of (R)-N-(benzyl)proline-derived glycine Schiff base Ni(II) complex

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Asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid by sequential S_N2–S_N2′ dialkylation of (R)-N-(benzyl)proline-derived glycine Schiff base Ni(ii) complex†

Asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid by sequential S_N2–S_N2′ dialkylation of (R)-N-(benzyl)proline-derived glycine Schiff base Ni(II) complex