Organocatalytic enantioselective Michael addition of β-diketones to β-nitrostyrene: The first Michael addition of dipivaloylmethane to an activated olefin

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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:	http://www.arkat-usa.org/
URI:	https://mu.eprints-hosting.org/id/eprint/3830
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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Organocatalytic enantioselective Michael addition of β-diketones to β-nitrostyrene: The first Michael addition of dipivaloylmethane to an activated olefin

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