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

31 January 2020, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

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.

Keywords

Vinyl Ethers
Hypervalent Iodine Compounds
Alkynes
Etherification

Supplementary materials

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Description
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Title
DW vinylether SI
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