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

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 th...

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Detalles Bibliográficos
Autores principales: Hodgson, David M, Xu, Zhaoqing
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2010
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2981828/
https://www.ncbi.nlm.nih.gov/pubmed/21085508
http://dx.doi.org/10.3762/bjoc.6.110
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author Hodgson, David M
Xu, Zhaoqing
author_facet Hodgson, David M
Xu, Zhaoqing
author_sort Hodgson, David M
collection PubMed
description 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.
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spelling pubmed-29818282010-11-17 α,β-Aziridinylphosphonates by lithium amide-induced phosphonyl migration from nitrogen to carbon in terminal aziridines Hodgson, David M Xu, Zhaoqing Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2010-10-13 /pmc/articles/PMC2981828/ /pubmed/21085508 http://dx.doi.org/10.3762/bjoc.6.110 Text en Copyright © 2010, Hodgson and Xu https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Hodgson, David M
Xu, Zhaoqing
α,β-Aziridinylphosphonates by lithium amide-induced phosphonyl migration from nitrogen to carbon in terminal aziridines
title α,β-Aziridinylphosphonates by lithium amide-induced phosphonyl migration from nitrogen to carbon in terminal aziridines
title_full α,β-Aziridinylphosphonates by lithium amide-induced phosphonyl migration from nitrogen to carbon in terminal aziridines
title_fullStr α,β-Aziridinylphosphonates by lithium amide-induced phosphonyl migration from nitrogen to carbon in terminal aziridines
title_full_unstemmed α,β-Aziridinylphosphonates by lithium amide-induced phosphonyl migration from nitrogen to carbon in terminal aziridines
title_short α,β-Aziridinylphosphonates by lithium amide-induced phosphonyl migration from nitrogen to carbon in terminal aziridines
title_sort α,β-aziridinylphosphonates by lithium amide-induced phosphonyl migration from nitrogen to carbon in terminal aziridines
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2981828/
https://www.ncbi.nlm.nih.gov/pubmed/21085508
http://dx.doi.org/10.3762/bjoc.6.110
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AT xuzhaoqing abaziridinylphosphonatesbylithiumamideinducedphosphonylmigrationfromnitrogentocarboninterminalaziridines

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