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

Markus Wiesner, Jefferson D. Revell, Sandro Tonazzi and Helma Wennemers

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

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

DOI: 10.1021/ja801027s


Abstract

The peptide H-D-Pro-Pro-Glu-NH2 is a highly effective catalyst for conjugate addition reactions between aldehydes and nitroethylene to obtain γ-nitroaldehydes and, after reduction, monosubstituted γ-nitroalcohols in excellent yields and optical purities. The products can be readily converted into γ2-amino acids that were previously only accessible by the use of chiral auxiliaries.

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

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


Key Words

Nitro Compounds, Organocatalysis


ID: J48-Y2008-1100