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Self-assembled ion-pair organocatalysis--asymmetric Baeyer-Villiger oxidation mediated by flavinium-cinchona alkaloid
Pramod Prasad Poudel1, Kenji Arimitsu1, Kana Yamamoto1
1Department of Chemistry and Biochemistry, University of Toledo, 2801 W. Bancroft St., Toledo, OH 43606, USA. kana.yamamoto@utoledo.edu.
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.
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