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

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• 作者：Markus Wiesner ; Jefferson D. Revell ; Sandro Tonazzi ; Helma Wennemers
• 刊名：Journal of the American Chemical Society
• 出版年：2008
• 出版时间：April 30, 2008
• 年：2008
• 卷：130
• 期：17
• 页码：5610 - 5611
• 全文大小：93K
• 年卷期：v.130,no.17(April 30, 2008)
• ISSN：1520-5126

文摘

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.