Catalytic generation of α-CF3 enolate: Direct catalytic asymmetric Mannich-type reaction of α-CF3 amide

Liang Yin, Lennart Brewitz, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

61 Citations (Scopus)

Abstract

The introduction of the CF3 unit is a common strategy for modifying pharmacokinetic properties and slowing metabolic degradation in medicinal chemistry. A catalytic and enantioselective addition of α-CF3 enolates allows for expeditious access to functionalized chiral building blocks with CF3-containing stereogenicity. To date, α-CF3 enolates have been a less explored class of nucleophiles because of rapid defluorination. The present study reveals that a designed α-CF3 amide enables a direct asymmetric Mannich-type reaction in a cooperative catalytic system.

Original languageEnglish
Pages (from-to)17958-17961
Number of pages4
JournalJournal of the American Chemical Society
Volume136
Issue number52
DOIs
Publication statusPublished - 2014 Dec 31
Externally publishedYes

ASJC Scopus subject areas

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

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