Simple catalytic mechanism for the direct coupling of α-carbonyls with functionalized amines: A one-step synthesis of plavix

Ryan W. Evans, Jason R. Zbieg, Shaolin Zhu, Wei Li, David W.C. Macmillan

Research output: Contribution to journalArticle

112 Scopus citations

Abstract

The direct α-amination of ketones, esters, and aldehydes has been accomplished via copper catalysis. In the presence of catalytic copper(II) bromide, a diverse range of carbonyl and amine substrates undergo fragment coupling to produce synthetically useful α-amino-substituted motifs. The transformation is proposed to proceed via a catalytically generated α-bromo carbonyl species; nucleophilic displacement of the bromide by the amine then delivers the α-amino carbonyl adduct while the catalyst is reconstituted. The practical value of this transformation is highlighted through one-step syntheses of two high-profile pharmaceutical agents, Plavix and amfepramone.

Original languageEnglish (US)
Pages (from-to)16074-16077
Number of pages4
JournalJournal of the American Chemical Society
Volume135
Issue number43
DOIs
StatePublished - Oct 30 2013

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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