Enantioselective fluorination mediated by cinchona alkaloid derivatives/Selectfluor combinations: Reaction scope and structural information for N-fluorocinchona alkaloids

N. Shibata, E. Suzuki, T. Asahi, M. Shiro

Research output: Contribution to journalArticle

229 Citations (Scopus)

Abstract

Cinchona-alkaloid/Selectfluor combinations efficiently fluorinate a variety of carbonyl compounds in a highly enantioselective manner to furnish chiral α-fluorocarbonyl compounds. The DHQB/Selectfluor combination is effective for the enantioselective fluorination of indanones and tetralones 1 in up to 91% ee. The first enantioselective syntheses of chiral derivatizing reagents 3 was accomplished with high ee and in high chemical yields by the DHQDA/Selectfluor combination. 3-Fluorooxindoles 7 were prepared with ee up to 83% using the (DHQ)2AQN/Selectfluor or the (DHQD)2PYR/Selectfluor combination. Since the combinations are conveniently prepared in situ from readily available reagents, the present system represents a practical method for enantioselective fluorination. X-ray crystallography and 1H NMR analyses of the cinchona alkaloids/Selectfluor combination have established that the species that mediate this novel reaction are N-fluoroammonium cinchona alkaloid tetrafluoroborates, which adopt open conformations.

Original languageEnglish
Pages (from-to)7001-7009
Number of pages9
JournalJournal of the American Chemical Society
Volume123
Issue number29
DOIs
Publication statusPublished - 2001 Oct 1

ASJC Scopus subject areas

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

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