Gavin, Declan P. and Stephens, John C.
Organocatalytic enantioselective Michael addition of β-diketones to β-nitrostyrene: The first Michael addition of dipivaloylmethane to an activated olefin.
ARKIVOC, 2011 (9).
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).
||The definitive version of this article with supplementary material is available at ARKIVOC Vol.2011 No.9 pp.407-421.
||Organocatalysis; nitrostyrene; β-diketones; Michael addition; bifunctional thiourea catalysts; cinchona alkaloids;
||Science & Engineering > Chemistry
Dr John Stephens
||22 Aug 2012 15:39
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