Catalytic asymmetric hydroxylation of α-alkoxycarbonyl amides with a Pr(OiPr)3/amide-based ligand catalyst

Sho Takechi, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

27 Citations (Scopus)

Abstract

A catalytic asymmetric hydroxylation of N-nonsubstituted α-alkoxycarbonyl amides is described. A new effective catalyst comprising Pr(OiPr)3 and a fluoro-substituted amide-based ligand was identified using oxaziridine as the oxidizing reagent. The catalyst components were in dynamic equilibrium in the reaction mixture, which assembled to form the associated transition state through metal coordination and hydrogen bonding.

Original languageEnglish
Pages (from-to)2140-2143
Number of pages4
JournalTetrahedron Letters
Volume52
Issue number17
DOIs
Publication statusPublished - 2011 Apr 27
Externally publishedYes

Keywords

  • Amide-based ligand
  • Asymmetric catalysis
  • Asymmetric hydroxylation
  • Rare earth metal
  • Tetrasubstituted stereogenic centers

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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