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

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-?,?-aziridinylphosphonates. The utility of this chemistry has been demonstrated in the asymmetric synthesis of a ?-aminophosphonate.

SUBMITTER: Hodgson DM

PROVIDER: S-EPMC2981828 | biostudies-literature | 2010 Oct

REPOSITORIES: biostudies-literature

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

Hodgson David M DM Xu Zhaoqing Z

Beilstein journal of organic chemistry 20101013

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. ...[more]

PMID: 21085508

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