Electrochemical selenium- and iodonium-initiated cyclisation of hydroxy-functionalised 1,4-dienes

The cobalt(I)-catalysed 1,4-hydrovinylation reaction of allyloxytrimethylsilane and allyl alcohol with substituted 1,3-dienes leads to hydroxy-functionalised 1,4-dienes in excellent regio- and diastereoselective fashion. Those 1,4-dienols can be converted into tetrahydrofuran and pyran derivatives u...

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Autores principales: Röse, Philipp, Emge, Steffen, Yoshida, Jun-ichi, Hilt, Gerhard
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4361995/
https://www.ncbi.nlm.nih.gov/pubmed/25815067
http://dx.doi.org/10.3762/bjoc.11.18
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author Röse, Philipp
Emge, Steffen
Yoshida, Jun-ichi
Hilt, Gerhard
author_facet Röse, Philipp
Emge, Steffen
Yoshida, Jun-ichi
Hilt, Gerhard
author_sort Röse, Philipp
collection PubMed
description The cobalt(I)-catalysed 1,4-hydrovinylation reaction of allyloxytrimethylsilane and allyl alcohol with substituted 1,3-dienes leads to hydroxy-functionalised 1,4-dienes in excellent regio- and diastereoselective fashion. Those 1,4-dienols can be converted into tetrahydrofuran and pyran derivatives under indirect electrochemical conditions generating selenium or iodonium cations. The reactions proceed in good yields and regioselectivities for the formation of single diastereomers.
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spelling pubmed-43619952015-03-26 Electrochemical selenium- and iodonium-initiated cyclisation of hydroxy-functionalised 1,4-dienes Röse, Philipp Emge, Steffen Yoshida, Jun-ichi Hilt, Gerhard Beilstein J Org Chem Full Research Paper The cobalt(I)-catalysed 1,4-hydrovinylation reaction of allyloxytrimethylsilane and allyl alcohol with substituted 1,3-dienes leads to hydroxy-functionalised 1,4-dienes in excellent regio- and diastereoselective fashion. Those 1,4-dienols can be converted into tetrahydrofuran and pyran derivatives under indirect electrochemical conditions generating selenium or iodonium cations. The reactions proceed in good yields and regioselectivities for the formation of single diastereomers. Beilstein-Institut 2015-01-28 /pmc/articles/PMC4361995/ /pubmed/25815067 http://dx.doi.org/10.3762/bjoc.11.18 Text en Copyright © 2015, Röse et al. 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
Röse, Philipp
Emge, Steffen
Yoshida, Jun-ichi
Hilt, Gerhard
Electrochemical selenium- and iodonium-initiated cyclisation of hydroxy-functionalised 1,4-dienes
title Electrochemical selenium- and iodonium-initiated cyclisation of hydroxy-functionalised 1,4-dienes
title_full Electrochemical selenium- and iodonium-initiated cyclisation of hydroxy-functionalised 1,4-dienes
title_fullStr Electrochemical selenium- and iodonium-initiated cyclisation of hydroxy-functionalised 1,4-dienes
title_full_unstemmed Electrochemical selenium- and iodonium-initiated cyclisation of hydroxy-functionalised 1,4-dienes
title_short Electrochemical selenium- and iodonium-initiated cyclisation of hydroxy-functionalised 1,4-dienes
title_sort electrochemical selenium- and iodonium-initiated cyclisation of hydroxy-functionalised 1,4-dienes
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4361995/
https://www.ncbi.nlm.nih.gov/pubmed/25815067
http://dx.doi.org/10.3762/bjoc.11.18
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AT hiltgerhard electrochemicalseleniumandiodoniuminitiatedcyclisationofhydroxyfunctionalised14dienes

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