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Issue 2, 2015
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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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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 (SN2), homogeneous SN2′ 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.

Graphical abstract: 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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Publication details

The article was received on 18 Oct 2014, accepted on 24 Nov 2014 and first published on 24 Nov 2014


Article type: Paper
DOI: 10.1039/C4RA12658K
RSC Adv., 2015,5, 1051-1058

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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

    A. Kawashima, C. Xie, H. Mei, R. Takeda, A. Kawamura, T. Sato, H. Moriwaki, K. Izawa, J. Han, J. L. Aceña and V. A. Soloshonok, RSC Adv., 2015, 5, 1051
    DOI: 10.1039/C4RA12658K

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