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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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Article information


Submitted
18 Oct 2014
Accepted
24 Nov 2014
First published
24 Nov 2014

RSC Adv., 2015,5, 1051-1058
Article type
Paper

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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