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Dual vicinal functionalisation of heterocycles via an interrupted Pummerer coupling/[3,3]-sigmatropic rearrangement cascade
A dual vicinal functionalisation cascade involving the union of heterocycles and allyl sulfoxides is described. In particular, the approach provides efficient one-step access to biologically relevant and synthetically important C3 thio, C2 carbo substituted indoles. The reaction operates under mild,...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5870476/ https://www.ncbi.nlm.nih.gov/pubmed/29629145 http://dx.doi.org/10.1039/c7sc04723a |
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author | Šiaučiulis, Mindaugas Sapmaz, Selma Pulis, Alexander P. Procter, David J. |
author_facet | Šiaučiulis, Mindaugas Sapmaz, Selma Pulis, Alexander P. Procter, David J. |
author_sort | Šiaučiulis, Mindaugas |
collection | PubMed |
description | A dual vicinal functionalisation cascade involving the union of heterocycles and allyl sulfoxides is described. In particular, the approach provides efficient one-step access to biologically relevant and synthetically important C3 thio, C2 carbo substituted indoles. The reaction operates under mild, metal free conditions and without directing groups, via an interrupted Pummerer coupling of activated allyl sulfoxides, generating allyl heteroaryl sulfonium salts that are predisposed to a charge accelerated [3,3]-sigmatropic rearrangement. |
format | Online Article Text |
id | pubmed-5870476 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-58704762018-04-06 Dual vicinal functionalisation of heterocycles via an interrupted Pummerer coupling/[3,3]-sigmatropic rearrangement cascade Šiaučiulis, Mindaugas Sapmaz, Selma Pulis, Alexander P. Procter, David J. Chem Sci Chemistry A dual vicinal functionalisation cascade involving the union of heterocycles and allyl sulfoxides is described. In particular, the approach provides efficient one-step access to biologically relevant and synthetically important C3 thio, C2 carbo substituted indoles. The reaction operates under mild, metal free conditions and without directing groups, via an interrupted Pummerer coupling of activated allyl sulfoxides, generating allyl heteroaryl sulfonium salts that are predisposed to a charge accelerated [3,3]-sigmatropic rearrangement. Royal Society of Chemistry 2017-11-17 /pmc/articles/PMC5870476/ /pubmed/29629145 http://dx.doi.org/10.1039/c7sc04723a Text en This journal is © The Royal Society of Chemistry 2018 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0) |
spellingShingle | Chemistry Šiaučiulis, Mindaugas Sapmaz, Selma Pulis, Alexander P. Procter, David J. Dual vicinal functionalisation of heterocycles via an interrupted Pummerer coupling/[3,3]-sigmatropic rearrangement cascade |
title | Dual vicinal functionalisation of heterocycles via an interrupted Pummerer coupling/[3,3]-sigmatropic rearrangement cascade
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title_full | Dual vicinal functionalisation of heterocycles via an interrupted Pummerer coupling/[3,3]-sigmatropic rearrangement cascade
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title_fullStr | Dual vicinal functionalisation of heterocycles via an interrupted Pummerer coupling/[3,3]-sigmatropic rearrangement cascade
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title_full_unstemmed | Dual vicinal functionalisation of heterocycles via an interrupted Pummerer coupling/[3,3]-sigmatropic rearrangement cascade
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title_short | Dual vicinal functionalisation of heterocycles via an interrupted Pummerer coupling/[3,3]-sigmatropic rearrangement cascade
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title_sort | dual vicinal functionalisation of heterocycles via an interrupted pummerer coupling/[3,3]-sigmatropic rearrangement cascade |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5870476/ https://www.ncbi.nlm.nih.gov/pubmed/29629145 http://dx.doi.org/10.1039/c7sc04723a |
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