Stereoselective access to highly substituted vinyl ethers via trans-difunctionalization of alkynes with alcohols and iodine(III) electrophile

Stereoselective access to highly substituted vinyl ethers via trans-difunctionalization of alkynes with alcohols and iodine(III) electrophile

A method for the regio- and stereoselective synthesis of highly substituted vinyl ethers via trans-1,2-difunctionalization of alkynes with a cyclic λ3-iodane electrophile (benziodoxole triflate) and alcohols is reported. The reaction tolerates a variety of internal and terminal alkynes as well as va...

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Main Authors: Ding, Wei, Chai, Jinkui, Wang, Chen, Wu, Junliang, Yoshikai, Naohiko
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2020
Subjects:
Science::Chemistry
Ethers
Hydrocarbons
Online Access:https://hdl.handle.net/10356/145625
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1456252023-02-28T19:53:58Z Stereoselective access to highly substituted vinyl ethers via trans-difunctionalization of alkynes with alcohols and iodine(III) electrophile Ding, Wei Chai, Jinkui Wang, Chen Wu, Junliang Yoshikai, Naohiko School of Physical and Mathematical Sciences Science::Chemistry Ethers Hydrocarbons A method for the regio- and stereoselective synthesis of highly substituted vinyl ethers via trans-1,2-difunctionalization of alkynes with a cyclic λ3-iodane electrophile (benziodoxole triflate) and alcohols is reported. The reaction tolerates a variety of internal and terminal alkynes as well as various alcohols, affording β-λ3-iodanyl vinyl ethers in good yields with high regio- and stereoselectivities. The benziodoxole moiety of the products can be used as a versatile linchpin for the synthesis of structurally diverse vinyl ethers that are difficult to access by other means. Ministry of Education (MOE) Accepted version This work was supported by the Ministry of Education(Singapore) and Nanyang Technological University(MOE2016-T2-2-043 and RG114/18). We thank Dr. Yongxin Li (Nanyang Technological University) for his assistance withthe X-ray crystallographic analysis. 2020-12-30T05:03:09Z 2020-12-30T05:03:09Z 2020 Journal Article Ding, W., Chai, J., Wang, C., Wu, J., & Yoshikai, N. (2020). Stereoselective access to highly substituted vinyl ethers via trans-difunctionalization of alkynes with alcohols and iodine(III) electrophile. Journal of the American Chemical Society, 142(19), 8619–8624. doi:10.1021/jacs.0c04140 0002-7863 https://hdl.handle.net/10356/145625 10.1021/jacs.0c04140 32362119 19 142 8619 8624 en Journal of the American Chemical Society This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/jacs.0c04140 application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Science::Chemistry
Ethers
Hydrocarbons
spellingShingle Science::Chemistry
Ethers
Hydrocarbons
Ding, Wei
Chai, Jinkui
Wang, Chen
Wu, Junliang
Yoshikai, Naohiko
Stereoselective access to highly substituted vinyl ethers via trans-difunctionalization of alkynes with alcohols and iodine(III) electrophile
description A method for the regio- and stereoselective synthesis of highly substituted vinyl ethers via trans-1,2-difunctionalization of alkynes with a cyclic λ3-iodane electrophile (benziodoxole triflate) and alcohols is reported. The reaction tolerates a variety of internal and terminal alkynes as well as various alcohols, affording β-λ3-iodanyl vinyl ethers in good yields with high regio- and stereoselectivities. The benziodoxole moiety of the products can be used as a versatile linchpin for the synthesis of structurally diverse vinyl ethers that are difficult to access by other means.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Ding, Wei
Chai, Jinkui
Wang, Chen
Wu, Junliang
Yoshikai, Naohiko
format Article
author Ding, Wei
Chai, Jinkui
Wang, Chen
Wu, Junliang
Yoshikai, Naohiko
author_sort Ding, Wei
title Stereoselective access to highly substituted vinyl ethers via trans-difunctionalization of alkynes with alcohols and iodine(III) electrophile
title_short Stereoselective access to highly substituted vinyl ethers via trans-difunctionalization of alkynes with alcohols and iodine(III) electrophile
title_full Stereoselective access to highly substituted vinyl ethers via trans-difunctionalization of alkynes with alcohols and iodine(III) electrophile
title_fullStr Stereoselective access to highly substituted vinyl ethers via trans-difunctionalization of alkynes with alcohols and iodine(III) electrophile
title_full_unstemmed Stereoselective access to highly substituted vinyl ethers via trans-difunctionalization of alkynes with alcohols and iodine(III) electrophile
title_sort stereoselective access to highly substituted vinyl ethers via trans-difunctionalization of alkynes with alcohols and iodine(iii) electrophile
publishDate 2020
url https://hdl.handle.net/10356/145625
_version_ 1759855011439837184

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