Triphenylphosphine as an effective catalyst for ketoximes addition to acylacetylenes: regio- and stereospecific synthesis of (E)-(O)-2-(acyl)vinylketoximes
Тип публикации: Journal Article
Дата публикации: 2010-09-01
scimago Q3
wos Q2
БС2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Краткое описание
Triphenylphosphine catalyzes the regio- and stereospecific addition of ketoximes to acylacetylenes, whereas classical conditions using acetylene (KOH/DMSO, 70 °C) are unsuitable for this purpose. The reaction proceeds under mild conditions (CH 2 Cl 2 , rt, 7 h) to afford ( E )-( O )-2-(acyl)vinylketoximes (92–98% stereoselectivity) in a yield of up to 85%. The ( E )-adducts obtained are energetically less favorable than the corresponding ( Z )-isomers and are gradually enriched with ( Z )-isomers, thus indicating the kinetic control of ( E )-stereoselectivity of the reaction.
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Trofimov B. A. et al. Triphenylphosphine as an effective catalyst for ketoximes addition to acylacetylenes: regio- and stereospecific synthesis of (E)-(O)-2-(acyl)vinylketoximes // Tetrahedron. 2010. Vol. 66. No. 38. pp. 7527-7532.
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Trofimov B. A., Glotova T. E., Dvorko M. Y., Ushakov I., Schmidt E. Yu., Mikhaleva A. I. Triphenylphosphine as an effective catalyst for ketoximes addition to acylacetylenes: regio- and stereospecific synthesis of (E)-(O)-2-(acyl)vinylketoximes // Tetrahedron. 2010. Vol. 66. No. 38. pp. 7527-7532.
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TY - JOUR
DO - 10.1016/j.tet.2010.07.057
UR - https://doi.org/10.1016/j.tet.2010.07.057
TI - Triphenylphosphine as an effective catalyst for ketoximes addition to acylacetylenes: regio- and stereospecific synthesis of (E)-(O)-2-(acyl)vinylketoximes
T2 - Tetrahedron
AU - Trofimov, B. A.
AU - Glotova, Tatyana E
AU - Dvorko, Marina Yu.
AU - Ushakov, Igor
AU - Schmidt, Elena Yu
AU - Mikhaleva, Al'bina I
PY - 2010
DA - 2010/09/01
PB - Elsevier
SP - 7527-7532
IS - 38
VL - 66
SN - 0040-4020
SN - 1464-5416
ER -
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@article{2010_Trofimov,
author = {B. A. Trofimov and Tatyana E Glotova and Marina Yu. Dvorko and Igor Ushakov and Elena Yu Schmidt and Al'bina I Mikhaleva},
title = {Triphenylphosphine as an effective catalyst for ketoximes addition to acylacetylenes: regio- and stereospecific synthesis of (E)-(O)-2-(acyl)vinylketoximes},
journal = {Tetrahedron},
year = {2010},
volume = {66},
publisher = {Elsevier},
month = {sep},
url = {https://doi.org/10.1016/j.tet.2010.07.057},
number = {38},
pages = {7527--7532},
doi = {10.1016/j.tet.2010.07.057}
}
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MLA
Скопировать
Trofimov, B. A., et al. “Triphenylphosphine as an effective catalyst for ketoximes addition to acylacetylenes: regio- and stereospecific synthesis of (E)-(O)-2-(acyl)vinylketoximes.” Tetrahedron, vol. 66, no. 38, Sep. 2010, pp. 7527-7532. https://doi.org/10.1016/j.tet.2010.07.057.
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