Enantioselective organocatalytic α-fluorination of cyclic ketones

Piotr Kwiatkowski, Teresa D. Beeson, Jay C. Conrad, David W.C. MacMillan

Research output: Contribution to journalArticle

154 Scopus citations

Abstract

The first highly enantioselective α-fluorination of ketones using organocatalysis has been accomplished. The long-standing problem of enantioselective ketone α-fluorination via enamine activation has been overcome via high-throughput evaluation of a new library of amine catalysts. The optimal system, a primary amine functionalized Cinchona alkaloid, allows the direct and asymmetric α-fluorination of a variety of carbo- and heterocyclic substrates. Furthermore, this protocol also provides diastereo-, regio-, and chemoselective catalyst control in fluorinations involving complex carbonyl systems.

Original languageEnglish (US)
Pages (from-to)1738-1741
Number of pages4
JournalJournal of the American Chemical Society
Volume133
Issue number6
DOIs
StatePublished - Feb 16 2011

All Science Journal Classification (ASJC) codes

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

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