Enamine Catalysis with Low Catalyst Loadings - High Efficiency via Kinetic Studies

Markus Wiesner, Grégory Upert, Gaetano Angelici and Helma Wennemers*

*Department of Chemistry, University of Basel, St. Johanns-Ring 19, CH-4056 Basel, Switzerland, Email: Helma.Wennemersunibas.ch

M. Wiesner, G. Upert, G. Angelici, H. Wennemers, J. Am. Chem. Soc., 2010, 132, 6-7.

DOI: 10.1021/ja9068112

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Abstract

Kinetic studies on enamine catalysis provided insight into the rate determining step(s) of conjugate addition reactions between aldehydes and nitroolefins. Not enamine formation but both the reaction of the enamine with the electrophile and hydrolysis of the resulting imine are rate limiting. These results enabled the reduction of the loading of the peptidic catalyst by a factor of 10.

see article for more examples

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Peptide Catalyzed Asymmetric Conjugate Addition Reactions of Aldehydes to Nitroethylene - A Convenient Entry into γ²-Amino Acids

M. Wiesner, J. D. Revell, S. Tonazzi, H. Wennemers, J. Am. Chem. Soc., 2008, 130, 5610-5611.

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Key Words

Nitro Compounds, Organocatalysis

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ID: J48-Y2010-0010