title: Self-assembled ion-pair organocatalysis--asymmetric Baeyer-Villiger oxidation mediated by flavinium-cinchona alkaloid dimer.
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.
authors.affiliation: Department of Chemistry and Biochemistry, University of Toledo, 2801 W. Bancroft St., Toledo, OH 43606, USA. kana.yamamoto@utoledo.edu.
authors.forename: Pramod Prasad
authors.initials: PP
authors.lastname: Poudel
authors.affiliation: Department of Chemistry and Biochemistry, University of Toledo, 2801 W. Bancroft St., Toledo, OH 43606, USA. kana.yamamoto@utoledo.edu.
authors.forename: Kenji
authors.initials: K
authors.lastname: Arimitsu
authors.affiliation: Department of Chemistry and Biochemistry, University of Toledo, 2801 W. Bancroft St., Toledo, OH 43606, USA. kana.yamamoto@utoledo.edu.
authors.forename: Kana
authors.initials: K
authors.lastname: Yamamoto
mesh_terms: D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry*; D019281:Dimerization; D047309:Flavones / Q000737:chemistry*; D007477:Ions; D010084:Oxidation-Reduction
chemical_list: D002930:Cinchona Alkaloids; D047309:Flavones; D007477:Ions