Beilstein journal of organic chemistry

α, β-Aziridinylphosphonates by lithium amide-induced phosphonyl migration from nitrogen to carbon in terminal aziridines

DM Hodgson, Z Xu

Index: Hodgson, DaviD. M.; Xu, Zhaoqing Beilstein Journal of Organic Chemistry, 2010 , vol. 6, p. 978 - 983

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Citation Number: 9

Abstract

Abstract N-Phosphonate terminal aziridines undergo lithium 2, 2, 6, 6-tetramethylpiperidide- induced N-to C-[1, 2]-anionic phosphonyl group migration under experimentally straightforward conditions, to provide a stereocontrolled access to synthetically valuable trans-α, β-aziridinylphosphonates. The utility of this chemistry has been demonstrated in the asymmetric synthesis of a β-aminophosphonate.