Asymmetric mannich reaction of fluorinated ketoesters with a tryptophan-derived bifunctional thiourea catalyst

Xiao Han*, Jacek Kwiatkowski, Teng Xue, Kuo-Wei Huang, Yixin Lu

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

164 Scopus citations

Abstract

Fluorinated quaternary stereocenters: A novel bifunctional catalyst 1 derived from natural tryptophan promoted the Mannich reaction of α-fluoro-β-ketoesters to afford fluorinated chiral molecules containing vicinal quaternary and tertiary stereogenic centers with exceptional enantioselectivity. An unprecedented α-fluoro-β -lactam was also prepared by this method (see scheme; Boc=tert-butoxycarbonyl).

Original languageEnglish (US)
Pages (from-to)7604-7607
Number of pages4
JournalAngewandte Chemie - International Edition
Volume48
Issue number41
DOIs
StatePublished - Sep 28 2009

Keywords

  • Asymmetric synthesis
  • Fluorination
  • Mannich reaction
  • Organocatalysis
  • Quaternary stereocenters

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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