Direct Catalytic Asymmetric Mannich-Type Reaction of an α-CF 3 Amide to Isatin Imines

Jin Sheng Yu, Hidetoshi Noda, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

Abstract

An α-CF 3 amide underwent direct asymmetric Mannich-type reaction to isatin imines in the presence of a chiral catalyst comprising a soft Lewis acid Cu(I), a chiral bisphosphine ligand, and Barton's base. The Mannich adduct was converted in one step into a unique tricycle bearing a trifluoromethylated chiral center and an α-tertiary amine moiety.

Original languageEnglish
Pages (from-to)488-492
Number of pages5
JournalSynlett
Volume30
Issue number4
DOIs
Publication statusPublished - 2019
Externally publishedYes

Keywords

  • asymmetric catalysis
  • copper catalysis
  • fluorine
  • heterocycle
  • Mannich reaction

ASJC Scopus subject areas

  • Organic Chemistry

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