Reaction of aryl(diarylphosphoryl)methanols with alkyl propiolates. Regio- and stereoselective synthesis of functional vinyl ethers

N. I. Ivanova; P. A. Volkov; K. O. Khrapova; L. I. Larina; I. Yu. Bagryanskaya; N. K. Gusarova; B. A. Trofimov

doi:10.1134/S1070428016060026

Reaction of aryl(diarylphosphoryl)methanols with alkyl propiolates. Regio- and stereoselective synthesis of functional vinyl ethers

Authors: Ivanova N.I.¹, Volkov P.A.¹, Khrapova K.O.¹, Larina L.I.¹, Bagryanskaya I.Y.²^,3, Gusarova N.K.¹, Trofimov B.A.¹
Affiliations:
1. Favorskii Irkutsk Institute of Chemistry, Siberian Branch
2. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch
3. Novosibirsk State University
Issue: Vol 52, No 6 (2016)
Pages: 772-776
Section: Article
URL: https://bakhtiniada.ru/1070-4280/article/view/214449
DOI: https://doi.org/10.1134/S1070428016060026
ID: 214449

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Abstract

Aryl(diarylphosphoryl)methanols reacted with alkyl propiolates under mild conditions (triethylamine, THF, 22‒25°C), to give the corresponding anti-Markovnikov adducts, alkyl (E)-3-[aryl(diarylphosphoryl) methoxy]prop-2-enoates, with high yields (84–90%) and regio- and stereoselectivity.