Metal-Controlled, Regioselective, Direct Intermolecular α- or γ-Amination with Azodicarboxylates.

A metal-controlled, regioselective intermolecular amination of unsaturated N-acylpyrazoles with azodicarboxylates is described. Under zinc catalysis, the N-acylpyrazole substrates undergo amination at the α-position of the N-acylpyrazole moiety. Conversely, with silver as the catalyst, the reaction gave γ-amination products. Both catalytic protocols provided alternative, convenient, and simple strategies for efficiently and regioselectively accessing structurally unique C-N-bond containing compounds. The synthetic utility of this method was illustrated by a gram-scale experiment and subsequent efficient synthesis of the γ-amino acid analogue.

• Publication year

  2018

• Venue

  Organic Letters

• Publication date

  2018-05-30

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/acs.orglett.8b01183PMID 29847138
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

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