Reaction of α,β-alkynylketones with β-amino alcohols: Pseudoephedrine- assisted cleavage of triple bond via formal internal redox process

Sergei F. Vasilevsky, Maria P. Davydova, Victor I. Mamatuyk, Nadezhda V. Pleshkova, Dmitry S. Fadeev, Igor V. Alabugin

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Abstract

Reaction of 3-aryl-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-ones with (+)-pseudoephedrine leads to products of alkyne moiety cleavage, namely, 1-(3,4,5-trimethoxyphenyl)ethanone and N-(1-hydroxy-1-phenylprop-2-yl)-N-methylbenzamides. In the course of the process one of alkyne carbons undergoes a formal reduction to a Me group, whereas the other one is oxidized to a C(O)NRR' moiety.

Original languageEnglish
Pages (from-to)377-379
Number of pages3
JournalMendeleev Communications
Volume25
Issue number5
DOIs
Publication statusPublished - 1 Sep 2015
Externally publishedYes

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ASJC Scopus subject areas

  • Chemistry(all)

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