Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2010, Issue 18, Pages 3449-3458Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201000273
Keywords
Asymmetric catalysis; Organocatalysis; Enantioselectivity; Regioselectivity; Ketones; Michael addition
Categories
Funding
- University of Aveiro
- Fundacao para a Ciencia e a Tecnologia (FCT)
- Fundo Europeu de Desenvolvimento Regional (FEDER)
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The development of general and efficient asymmetric organocatalytic additions of malononitrile and nitromethane to 1,5-diarylpenta-2,4-dien-1-ones (cinnamylideneacetophenones) catalyzed by cinchona organocatalysts is reported. The reactions afforded excellent enantioselectivities (up to 99%), high yields (up to 97%), and exclusive 1,4-addition regioselectivities. The potential of these new enantioselective additions lies in the demonstration that organocatalysts bearing primary amino groups in combination with TFA provide effective catalytic systems for the activation of a broad range of aryl ketones under mild conditions to give compounds with high levels of enantioselectivity and yields.
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