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

Pramod Prasad Poudel; Kenji Arimitsu; Kana Yamamoto

doi:10.1039/c6cc00663a

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

Pramod Prasad Poudel, Kenji Arimitsu, Kana Yamamoto^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

32 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 language	English
Pages (from-to)	4163-4166
Number of pages	4
Journal	Chemical Communications
Volume	52
Issue number	22
DOIs	https://doi.org/10.1039/c6cc00663a
Publication status	Published - 2016 Mar 18
Externally published	Yes

ASJC Scopus subject areas

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

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AU - Arimitsu, Kenji

AU - Yamamoto, Kana

N1 - Publisher Copyright: © The Royal Society of Chemistry 2016.

PY - 2016/3/18

Y1 - 2016/3/18

N2 - 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.

AB - 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.

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

Abstract

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