Synthesis and ring openings of cinnamate-derived N-unfunctionalised aziridines

tert-Butyl cinnamates are aziridinated with high trans-selectivity by an N–N ylide generated in situ from N-methylmorpholine and O-diphenylphosphinyl hydroxylamine. The resulting N-unfunctionalised aziridines are shown to be versatile synthetic building blocks that undergo highly selective ring-open...

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Detalles Bibliográficos
Autores principales: Armstrong, Alan, Ferguson, Alexandra
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2012
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3511008/
https://www.ncbi.nlm.nih.gov/pubmed/23209508
http://dx.doi.org/10.3762/bjoc.8.199
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author Armstrong, Alan
Ferguson, Alexandra
author_facet Armstrong, Alan
Ferguson, Alexandra
author_sort Armstrong, Alan
collection PubMed
description tert-Butyl cinnamates are aziridinated with high trans-selectivity by an N–N ylide generated in situ from N-methylmorpholine and O-diphenylphosphinyl hydroxylamine. The resulting N-unfunctionalised aziridines are shown to be versatile synthetic building blocks that undergo highly selective ring-opening reactions with a wide range of nucleophiles.
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spelling pubmed-35110082012-12-03 Synthesis and ring openings of cinnamate-derived N-unfunctionalised aziridines Armstrong, Alan Ferguson, Alexandra Beilstein J Org Chem Full Research Paper tert-Butyl cinnamates are aziridinated with high trans-selectivity by an N–N ylide generated in situ from N-methylmorpholine and O-diphenylphosphinyl hydroxylamine. The resulting N-unfunctionalised aziridines are shown to be versatile synthetic building blocks that undergo highly selective ring-opening reactions with a wide range of nucleophiles. Beilstein-Institut 2012-10-12 /pmc/articles/PMC3511008/ /pubmed/23209508 http://dx.doi.org/10.3762/bjoc.8.199 Text en Copyright © 2012, Armstrong and Ferguson 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
Armstrong, Alan
Ferguson, Alexandra
Synthesis and ring openings of cinnamate-derived N-unfunctionalised aziridines
title Synthesis and ring openings of cinnamate-derived N-unfunctionalised aziridines
title_full Synthesis and ring openings of cinnamate-derived N-unfunctionalised aziridines
title_fullStr Synthesis and ring openings of cinnamate-derived N-unfunctionalised aziridines
title_full_unstemmed Synthesis and ring openings of cinnamate-derived N-unfunctionalised aziridines
title_short Synthesis and ring openings of cinnamate-derived N-unfunctionalised aziridines
title_sort synthesis and ring openings of cinnamate-derived n-unfunctionalised aziridines
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3511008/
https://www.ncbi.nlm.nih.gov/pubmed/23209508
http://dx.doi.org/10.3762/bjoc.8.199
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AT fergusonalexandra synthesisandringopeningsofcinnamatederivednunfunctionalisedaziridines

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