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Highly efficient and enantioselective Michael addition of acetylacetone to nitroolefins catalyzed by chiral bifunctional organocatalyst bearing multiple hydrogen-bonding donors

✍ Scribed by Xin Shi; Wei He; Hua Li; Xu Zhang; Shengyong Zhang

Book ID: 104099183
Publisher: Elsevier Science
Year: 2011
Tongue: French
Weight: 446 KB
Volume: 52
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2011.04.043

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✦ Synopsis

A new efficient catalyst system for the asymmetric addition of acetylacetone to nitroolefins using a chiral bifunctional organocatalyst bearing multiple hydrogen-bonding donors was developed. When using the organocatalyst 2c derived from natural cinchona alkaloid in optimal conditions, up to 98% chemical yield and 98% ee were observed with a variety of aromatic nitroolefins.

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