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Cesium Carbonate Catalyzed Oxa‐Michael Addition of Oximes to Acrylonitrile
Stahl, Jessica, Yatham, Veera Reddy
, Crespi, Stefano and König, Burkhard
(2021)
Cesium Carbonate Catalyzed Oxa‐Michael Addition of Oximes to Acrylonitrile.
ChemistrySelect 6, pp. 4107-4111.
Date of publication of this fulltext: 14 May 2021 04:17
Article
DOI to cite this document: 10.5283/epub.45689
Abstract
We report the O-alkylation of oximes with Michael acceptors using Cs2CO3 as the catalyst. The transformation proceeds stereospecifically with retention of the oxime configuration. Irradiation with visible light in the presence of diphenyl anthracene and cerium complexes affects the E to Z configuration ratio of the oxime ether products, but a complete stereocontrol was not achieved. The ...
We report the O-alkylation of oximes with Michael acceptors using Cs2CO3 as the catalyst. The transformation proceeds stereospecifically with retention of the oxime configuration. Irradiation with visible light in the presence of diphenyl anthracene and cerium complexes affects the E to Z configuration ratio of the oxime ether products, but a complete stereocontrol was not achieved. The operationally simple protocol allows the synthesis of various O-alkylated oxime products that are useful precursors for further chemical transformations.
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| Item type | Article | ||||
| Journal or Publication Title | ChemistrySelect | ||||
| Publisher: | Wiley | ||||
|---|---|---|---|---|---|
| Place of Publication: | WEINHEIM | ||||
| Volume: | 6 | ||||
| Page Range: | pp. 4107-4111 | ||||
| Date | 2021 | ||||
| Institutions | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König | ||||
| Identification Number |
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| Keywords | INORGANIC BASE; ISOMERIZATION; ACID; PHOTOISOMERIZATION; ESTERS; Cesium carbonate catalyst; Lewis acids; Oxa-Michael addition; Photochemistry; Stereoisomers | ||||
| Dewey Decimal Classification | 500 Science > 540 Chemistry & allied sciences | ||||
| Status | Published | ||||
| Refereed | Yes, this version has been refereed | ||||
| Created at the University of Regensburg | Partially | ||||
| URN of the UB Regensburg | urn:nbn:de:bvb:355-epub-456895 | ||||
| Item ID | 45689 |
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