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Highly Enantioselective 1,4-Michael Additions of Nucleophiles to Unsaturated Aryl Ketones with Organocatalysis by Bifunctional Cinchona Alkaloids

✍ Scribed by Cristina G. Oliva; Artur M. S. Silva; Diana I. S. P. Resende; Filipe A. A. Paz; José A. S. Cavaleiro

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
396 KB
Volume
2010
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

The development of general and efficient asymmetricorganocatalytic 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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