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release of an aryl methyl ketone. The absence of hemiaminal 8 in
mixtures suggest that its fragmentation proceeds faster than its
formation via addition of water to amino enone 5. The relatively
slow rate of this step explains why compound 5a was isolated
whereas 5b and 5c were not observed. In the case of 5a, the
donor group at the aromatic ring (R = OMe) would deactivate its
double bond.
In summary, we have described a pseudoephedrine-assisted
cleavage of all three C–C bonds in a polarized alkyne moiety
of 1,3-diarylprop-2-yn-1-ones, leading to the corresponding
aryl methyl ketone and N-(1-hydroxy-1-phenylprop-2-yl)-4-R-
N-methylbenzamides. In the overall process, one of the alkyne
carbons undergoes formal reduction with the formation of three
C–H bonds, whereas the other carbon undergoes formal oxida-
tion via the formation of one C–N bond and carbonyl (C=O)
moiety.
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This work was supported by the Russian Foundation for Basic
Research (grant no. 13-03-00129), RussianAcademy of Sciences
(grant no. 5.9.3, 2014), grant of the Ministry of Education and
Science of the Russian Federation (2014–2016) and the Chemical
Service Centre of SB RAS. Research at FSU was supported by
the National Science Foundation (CHE-1465142).
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133, 12608.
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Online Supplementary Materials
Supplementary data associated with this article can be found
in the online version at doi:10.1016/j.mencom.2015.09.021.
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7 A. S. Zanina, S. I. Shergina, I. E. Sokolov and R. N. Myasnikova, Russ.
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Received: 4th March 2015; Com. 15/4578
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