Cargando…

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,...

Descripción completa

Detalles Bibliográficos
Autores principales: Šiaučiulis, Mindaugas, Sapmaz, Selma, Pulis, Alexander P., Procter, David J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
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
_version_ 1783309491517784064
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
title_full Dual vicinal functionalisation of heterocycles via an interrupted Pummerer coupling/[3,3]-sigmatropic rearrangement cascade
title_fullStr Dual vicinal functionalisation of heterocycles via an interrupted Pummerer coupling/[3,3]-sigmatropic rearrangement cascade
title_full_unstemmed Dual vicinal functionalisation of heterocycles via an interrupted Pummerer coupling/[3,3]-sigmatropic rearrangement cascade
title_short Dual vicinal functionalisation of heterocycles via an interrupted Pummerer coupling/[3,3]-sigmatropic rearrangement cascade
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
work_keys_str_mv AT siauciulismindaugas dualvicinalfunctionalisationofheterocyclesviaaninterruptedpummerercoupling33sigmatropicrearrangementcascade
AT sapmazselma dualvicinalfunctionalisationofheterocyclesviaaninterruptedpummerercoupling33sigmatropicrearrangementcascade
AT pulisalexanderp dualvicinalfunctionalisationofheterocyclesviaaninterruptedpummerercoupling33sigmatropicrearrangementcascade
AT procterdavidj dualvicinalfunctionalisationofheterocyclesviaaninterruptedpummerercoupling33sigmatropicrearrangementcascade