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Triphenylphosphine as an effective catalyst for ketoximes addition to acylacetylenes: regio- and stereospecific synthesis of (E)-(O)-2-(acyl)vinylketoximes
- Source :
-
Tetrahedron . Sep2010, Vol. 66 Issue 38, p7527-7532. 6p. - Publication Year :
- 2010
-
Abstract
- Abstract: 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 (CH2Cl2, rt, 7h) 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. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00404020
- Volume :
- 66
- Issue :
- 38
- Database :
- Academic Search Index
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 53332186
- Full Text :
- https://doi.org/10.1016/j.tet.2010.07.057