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Stereoselective Access to Highly Substituted Vinyl Ethers via Trans-Difunctionalization of Alkynes with Alcohols and Iodine(III) Electrophile

preprint
submitted on 30.01.2020 and posted on 31.01.2020 by Wei Ding, Jinkui Chai, Junliang Wu, Naohiko Yoshikai
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.

Funding

MOE2016-T2-2-043/Ministry of Education (Singapore)

RG114/18/Ministry of Education (Singapore)

History

Email Address of Submitting Author

nyoshikai@ntu.edu.sg

Institution

Nanyang Technological University

Country

Singapore

ORCID For Submitting Author

0000-0002-8997-3268

Declaration of Conflict of Interest

No conflict of interest

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