Self-assembled ion-pair organocatalysis - Asymmetric Baeyer-Villiger oxidation mediated by flavinium-cinchona alkaloid dimer

Pramod Prasad Poudel, Kenji Arimitsu, Kana Yamamoto

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

An ion-pair catalyst generated by assembly of a chiral flavinium and a cinchona alkaloid dimer for use in asymmetric Baeyer-Villiger oxidation is presented. Ion-pair formation is essential for enhancing the catalytic activity and stereoselectivity. The catalyst is applicable to structurally diverse 3-substituted cyclobutanones, providing good to excellent enantioselectivities (up to 98: 2 e.r.). This study provides the first example of self-assembly of a flavin derivative and a base to form a chiral reaction site that enables a highly stereoselective reaction to occur.

Original languageEnglish
Pages (from-to)4163-4166
Number of pages4
JournalChemical Communications
Volume52
Issue number22
DOIs
Publication statusPublished - 2016 Mar 18
Externally publishedYes

Fingerprint

Cinchona Alkaloids
Dimers
Ions
Stereoselectivity
Oxidation
Catalysts
Enantioselectivity
Self assembly
Catalyst activity
Derivatives

ASJC Scopus subject areas

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

Cite this

Self-assembled ion-pair organocatalysis - Asymmetric Baeyer-Villiger oxidation mediated by flavinium-cinchona alkaloid dimer. / Poudel, Pramod Prasad; Arimitsu, Kenji; Yamamoto, Kana.

In: Chemical Communications, Vol. 52, No. 22, 18.03.2016, p. 4163-4166.

Research output: Contribution to journalArticle

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