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

作者:Kawashima Aki; Xie Chen; Mei Haibo; Takeda Ryosuke; Kawamura Akie; Sato Tatsunori; Moriwaki Hiroki; Izawa Kunisuke; Han Jianlin*; Luis Acena Jose; Soloshonok Vadim A
来源:RSC Advances, 2015, 5(2): 1051-1058.
DOI:10.1039/c4ra12658k

摘要

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(N)2), homogeneous S(N)2' 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.