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Communication

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

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

Department of Chemistry, University of Basel, St. Johanns-Ring 19, CH-4056 Basel, Switzerland

J. Am. Chem. Soc., 2008, 130 (17), pp 5610–5611

DOI: 10.1021/ja801027s

Publication Date (Web): April 4, 2008

Abstract

The peptide H-d-Pro-Pro-Glu-NH₂ is a highly effective catalyst for conjugate addition reactions between aldehydes and nitroethylene. Only 1 mol % of H-d-Pro-Pro-Glu-NH₂ and a 1.5-fold excess of aldehyde with respect to nitroethylene suffice 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, thereby opening an effective direct entry into this important class of compounds.

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History

Published In Issue April 30, 2008
Article ASAPApril 04, 2008
Received: February 10, 2008

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Communication

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