Copper(i) catalyzed oxidative hydrolysis of Ugi 3-component and Ugi-azide reaction products towards 2° α-ketoamides and α-ketotetrazoles

Jurriën W. Collet, Christopher Foley, Arthur Y. Shaw, Romano V.A. Orru, Eelco Ruijter, Christopher Hulme

Research output: Contribution to journalArticle

6 Scopus citations

Abstract

Herein, a two-step MCR-oxidation methodology accessing decorated 2° α-ketoamides and α-ketotetrazoles is described via a catalytic copper(i)-mediated C-N oxidation/acidic hydrolysis of Ugi-three-component and Ugi-azide reaction products. The ability to install diversity from aldehyde and isocyanide synthons allows rapid complexity generation. Of note, (1) 2° α-ketoamides are traditionally difficult to access and more so reminiscent of the endogenous peptide bonds. (2) The route to α-keto-tetrazoles is significantly shorter than that in previous reports.

Original languageEnglish (US)
Pages (from-to)6132-6135
Number of pages4
JournalOrganic and Biomolecular Chemistry
Volume15
Issue number29
DOIs
StatePublished - 2017

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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