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