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Gavin, Declan P. and Stephens, John C. (2011) Organocatalytic enantioselective Michael addition of β-diketones to β-nitrostyrene: The first Michael addition of dipivaloylmethane to an activated olefin. ARKIVOC, 2011 (9). pp. 407-421. ISSN 1551-7012
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Abstract
The addition of a family of β-diketones to β-nitrostyrene was explored using a library of cinchona organocatalysts. A thiourea organocatalyst, under improved reaction conditions, is shown to be much more efficient at catalyzing this reaction than previously reported giving excellent yields and enantioselectivites (up to 95% yield and 97% ee). The same thiourea organocatalyst was employed in the first successful Michael addition of the sterically challenging dipivaloylmethane to β-nitrostyrene (99% ee).
| Item Type: | Article |
|---|---|
| Additional Information: | The definitive version of this article with supplementary material is available at ARKIVOC Vol.2011 No.9 pp.407-421. |
| Keywords: | Organocatalysis; nitrostyrene; β-diketones; Michael addition; bifunctional thiourea catalysts; cinchona alkaloids; |
| Academic Unit: | Faculty of Science and Engineering > Chemistry |
| Item ID: | 3830 |
| Depositing User: | Dr John Stephens |
| Date Deposited: | 22 Aug 2012 15:39 |
| Journal or Publication Title: | ARKIVOC |
| Publisher: | ARKAT-USA |
| Refereed: | Yes |
| Related URLs: | |
| Use Licence: | This item is available under a Creative Commons Attribution Non Commercial Share Alike Licence (CC BY-NC-SA). Details of this licence are available here |
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