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

Wei Ding; Jinkui Chai; Chen Wang; Junliang Wu; Naohiko Yoshikai

doi:10.1021/jacs.0c04140

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

Wei Ding, Jinkui Chai, Chen Wang, Junliang Wu, Naohiko Yoshikai

Research output: Contribution to journal › Article › peer-review

22 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	8619-8624
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	142
Issue number	19
DOIs	https://doi.org/10.1021/jacs.0c04140
Publication status	Published - 2020 May 13
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.0c04140

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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.

In: Journal of the American Chemical Society, Vol. 142, No. 19, 13.05.2020, p. 8619-8624.

Research output: Contribution to journal › Article › peer-review

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title = "Stereoselective access to highly substituted vinyl ethers via trans-difunctionalization of alkynes with alcohols and iodine(iii) electrophile",

abstract = "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.",

author = "Wei Ding and Jinkui Chai and Chen Wang and Junliang Wu and Naohiko Yoshikai",

note = "Funding Information: 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 with the X-ray crystallographic analysis. Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",

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AU - Chai, Jinkui

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AU - Wu, Junliang

AU - Yoshikai, Naohiko

N1 - Funding Information: 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 with the X-ray crystallographic analysis. Publisher Copyright: © 2020 American Chemical Society.

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AB - 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.

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

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