Flavin–cyclodextrin conjugates: effect of the structure on the catalytic activity in enantioselective sulfoxidations |
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Authors: | Tomá? Hartman Vladimír Herzig Milo? Budě?ínský Jind?ich Jind?ich Radek Cibulka Tomá? Kraus |
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Institution: | 1. Department of Organic Chemistry, Institute of Chemical Technology, Prague, Technická 5, Prague 6, Czech Republic;2. Institute of Organic Chemistry and Biochemistry AS CR, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic;3. Department of Organic Chemistry, Charles University in Prague, Faculty of Science, Hlavova 2030, 128 40 Prague 2, Czech Republic |
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Abstract: | A series of flavin–cyclodextrin conjugates has been prepared and tested in the enantioselective oxidations of prochiral aromatic and aliphatic sulfides with hydrogen peroxide. The newly prepared conjugates contain isoalloxazinium or alloxazinium moieties attached to the primary rim of α- and β-cyclodextrins at the C-6 positions. In addition, flavinium units were attached to the secondary rim of the β-cyclodextrin macrocycle. The relationship between the structural features and the catalytic performance of the conjugates, including those recently reported by us, was analyzed. The rate and enantioselectivity of the sulfoxidations catalyzed by flavin–cyclodextrin conjugates are influenced mainly by the size of the cyclodextrin cavity, the type of flavin unit (alloxazine or isoalloxazine), and by the relative orientation of the flavin and cyclodextrin moieties. |
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