Bifunctional cinchona alkaloid thiourea catalyzed highly efficient, enantioselective aza-henry reaction of cyclic trifluoromethyl ketimines: Synthesis of anti-HIV drug DPC 083

Hexin Xie, Yinan Zhang, Shilei Zhang, Xiaobei Chen, Wei Wang

Research output: Contribution to journalArticlepeer-review

127 Scopus citations

Abstract

Highly efficient: The title reaction provides biologically interesting chiral trifluoromethyl dihydroquinazolinone frameworks in high yields (up to 97%) and with high enantioselectivities (up to 98% ee), using as low as 1 mol% of catalyst (see scheme). Moreover, anti-HIV drug candidate DPC 083 was efficiently synthesized using the highly enantioselective aza-Henry reaction as a key step.

Original languageEnglish (US)
Pages (from-to)11773-11776
Number of pages4
JournalAngewandte Chemie - International Edition
Volume50
Issue number49
DOIs
StatePublished - Dec 2 2011
Externally publishedYes

Keywords

  • alkaloids
  • asymmetric synthesis
  • aza-Henry reaction
  • drug synthesis
  • organocatalysis

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry

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