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Bi(OTf)(3)-catalysed intramolecular cyclisation of unsaturated acetals

A series of highly functionalized carbocycles was efficiently prepared via the selective cyclisation of unsaturated acetals and ketals in the presence of only 1 mol% of Bi(iii) or Fe(iii) triflates as the catalysts at room temperature, with yields ranging from 60 to 90%. With Bi(OTf)(3) catalysis, α...

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Detalles Bibliográficos
Autores principales: Saget, Raphaël, Jaunky, Piotr, Duñach, Elisabet
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9034051/
https://www.ncbi.nlm.nih.gov/pubmed/35479394
http://dx.doi.org/10.1039/d1ra03686f
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author Saget, Raphaël
Jaunky, Piotr
Duñach, Elisabet
author_facet Saget, Raphaël
Jaunky, Piotr
Duñach, Elisabet
author_sort Saget, Raphaël
collection PubMed
description A series of highly functionalized carbocycles was efficiently prepared via the selective cyclisation of unsaturated acetals and ketals in the presence of only 1 mol% of Bi(iii) or Fe(iii) triflates as the catalysts at room temperature, with yields ranging from 60 to 90%. With Bi(OTf)(3) catalysis, α,β-unsaturated ether carbocycles are formed selectively, whereas with the Fe(OTf)(3) system, a cycloisomerisation to carbocyclic diethers is mainly obtained. This acetal/olefin cyclisation could be run at a multi-gram scale and compound 2c could be obtained on a 300 gram-scale with a yield of 69% after precipitation in hexane.
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spelling pubmed-90340512022-04-26 Bi(OTf)(3)-catalysed intramolecular cyclisation of unsaturated acetals Saget, Raphaël Jaunky, Piotr Duñach, Elisabet RSC Adv Chemistry A series of highly functionalized carbocycles was efficiently prepared via the selective cyclisation of unsaturated acetals and ketals in the presence of only 1 mol% of Bi(iii) or Fe(iii) triflates as the catalysts at room temperature, with yields ranging from 60 to 90%. With Bi(OTf)(3) catalysis, α,β-unsaturated ether carbocycles are formed selectively, whereas with the Fe(OTf)(3) system, a cycloisomerisation to carbocyclic diethers is mainly obtained. This acetal/olefin cyclisation could be run at a multi-gram scale and compound 2c could be obtained on a 300 gram-scale with a yield of 69% after precipitation in hexane. The Royal Society of Chemistry 2021-06-14 /pmc/articles/PMC9034051/ /pubmed/35479394 http://dx.doi.org/10.1039/d1ra03686f Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Saget, Raphaël
Jaunky, Piotr
Duñach, Elisabet
Bi(OTf)(3)-catalysed intramolecular cyclisation of unsaturated acetals
title Bi(OTf)(3)-catalysed intramolecular cyclisation of unsaturated acetals
title_full Bi(OTf)(3)-catalysed intramolecular cyclisation of unsaturated acetals
title_fullStr Bi(OTf)(3)-catalysed intramolecular cyclisation of unsaturated acetals
title_full_unstemmed Bi(OTf)(3)-catalysed intramolecular cyclisation of unsaturated acetals
title_short Bi(OTf)(3)-catalysed intramolecular cyclisation of unsaturated acetals
title_sort bi(otf)(3)-catalysed intramolecular cyclisation of unsaturated acetals
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9034051/
https://www.ncbi.nlm.nih.gov/pubmed/35479394
http://dx.doi.org/10.1039/d1ra03686f
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