Reaction of alpha,beta-alkynylketones with beta-amino alcohols: pseudoephedrine-assisted cleavage of triple bond via formal internal redox process

Reaction of alpha,beta-alkynylketones with beta-amino alcohols: pseudoephedrine-assisted cleavage of triple bond via formal internal redox process Full article

Journal

Mendeleev Communications
ISSN: 0959-9436

Output data

Year: 2015, Volume: 25, Number: 5, Pages: 377-379 Pages count : DOI: 10.1016/j.mencom.2015.09.021

Authors

Vasievsky Sergei F. ^1,2 , Davydova Maria P. ¹ , Mamatuyk Victor I. ^2,3 , Pleshkova Nadezhda V. ³ , Fadeev Dmitry S. ³ , Alabugin Igor V. ⁴

Affiliations

1	(Данные Web of science) Russian Acad Sci, VV Voevodsky Inst Chem Kinet & Combust, Siberian Branch, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Dept Nat Sci, Novosibirsk 630090, Russia
3	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, Novosibirsk 630090, Russia
4	(Данные Web of science) Florida State Univ, Dept Chem & Biochem, Tallahassee, FL 32306 USA

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.

Vasievsky S.F. , Davydova M.P. , Mamatuyk V.I. , Pleshkova N.V. , Fadeev D.S. , Alabugin I.V.
Reaction of alpha,beta-alkynylketones with beta-amino alcohols: pseudoephedrine-assisted cleavage of triple bond via formal internal redox process
Mendeleev Communications. 2015. V.25. N5. P.377-379. DOI: 10.1016/j.mencom.2015.09.021 WOS Scopus РИНЦ

Published print:

Sep 1, 2015

Web of science	WOS:000363350500021
Scopus	2-s2.0-84943257354
Elibrary	24959234
OpenAlex	W2197987278