4.8 Article

Chiral π-Cu(II) Catalysts for the Enantioselective α-Amination of N-Acyl-3,5-dimethylpyrazoles

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ORGANIC LETTERS
卷 24, 期 41, 页码 7685-7689

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c03249

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资金

  1. JSPS KAKENHI [JP15H05755, JP15H05810]
  2. NOVARTIS Foundation (Japan) for the Promotion of Science
  3. Nagoya University Research Fund
  4. China Scholarship Council

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A highly enantioselective alpha-amination reaction is reported, where N-acyl-3,5-dimethylpyrazoles react with dialkyl azodicarboxylates catalyzed by in situ generated pi-Cu(II) complexes. The corresponding D-alpha-amino acid derivatives are obtained with high yield and enantiopurity.
We report the highly enantioselective alpha-amination of N- acyl-3,5-dimethylpyrazoles with dialkyl azodicarboxylates, catalyzed by in situ generated pi-Cu(II) complexes that consist of Cu(OTf)2 and N- (5H-dibenzo[a,d][7]annulen-5-yl)-L-alanine-derived amides, to give the corresponding products as D-alpha-amino acid derivatives (up to >99% yield and 99% ee). The site-selectivity and enantioselectivity can be satisfactorily explained by the coordination of dialkyl azodicarboxylate with pi-Cu(II) complex. The synthetic potential of this one-pot transformation to the alpha-amino ester is also described.

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