期刊
TETRAHEDRON
卷 66, 期 38, 页码 7527-7532出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.07.057
关键词
Oximes; Acylacetylenes; Triphenylphosphine; O-vinylation; Isomerization
资金
- President of the Russian Federation [NSH 3230-2010.3]
Triphenylphosphine catalyzes the regio- and stereospecific addition of ketoximes to acylacetylenes, whereas classical conditions using acetylene (KOH/DMSO, 70 degrees C) are unsuitable for this purpose. The reaction proceeds under mild conditions (CH2Cl2, 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. (C) 2010 Elsevier Ltd. All rights reserved.
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