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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Main Authors:	Philipp Röse, Steffen Emge, Jun-ichi Yoshida, Gerhard Hilt
Format:	Article
Language:	English
Published:	Beilstein-Institut 2015-01-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	cyclic ethers cyclisation 1,4-dienes electrochemistry iodonium selenium
Online Access:	https://doi.org/10.3762/bjoc.11.18

id	doaj-18a671a0195148979d1bce42bf1aac95
record_format	Article
spelling	doaj-18a671a0195148979d1bce42bf1aac952021-04-02T10:09:35ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972015-01-0111117418310.3762/bjoc.11.181860-5397-11-18Electrochemical selenium- and iodonium-initiated cyclisation of hydroxy-functionalised 1,4-dienesPhilipp Röse0Steffen Emge1Jun-ichi Yoshida2Gerhard Hilt3Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Str. 4, 35043 Marburg, GermanyFachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Str. 4, 35043 Marburg, GermanyDepartment of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, JapanFachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Str. 4, 35043 Marburg, GermanyThe 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.https://doi.org/10.3762/bjoc.11.18cyclic etherscyclisation1,4-dieneselectrochemistryiodoniumselenium
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Philipp Röse Steffen Emge Jun-ichi Yoshida Gerhard Hilt
spellingShingle	Philipp Röse Steffen Emge Jun-ichi Yoshida Gerhard Hilt Electrochemical selenium- and iodonium-initiated cyclisation of hydroxy-functionalised 1,4-dienes Beilstein Journal of Organic Chemistry cyclic ethers cyclisation 1,4-dienes electrochemistry iodonium selenium
author_facet	Philipp Röse Steffen Emge Jun-ichi Yoshida Gerhard Hilt
author_sort	Philipp Röse
title	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_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_sort	electrochemical selenium- and iodonium-initiated cyclisation of hydroxy-functionalised 1,4-dienes
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2015-01-01
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.
topic	cyclic ethers cyclisation 1,4-dienes electrochemistry iodonium selenium
url	https://doi.org/10.3762/bjoc.11.18
work_keys_str_mv	AT philipprose electrochemicalseleniumandiodoniuminitiatedcyclisationofhydroxyfunctionalised14dienes AT steffenemge electrochemicalseleniumandiodoniuminitiatedcyclisationofhydroxyfunctionalised14dienes AT junichiyoshida electrochemicalseleniumandiodoniuminitiatedcyclisationofhydroxyfunctionalised14dienes AT gerhardhilt electrochemicalseleniumandiodoniuminitiatedcyclisationofhydroxyfunctionalised14dienes
_version_	1724167800013979648

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

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