Capping Methodology in Cyclodextrin Chemistry: Use of a Symmetrical Diketone Reagent for Regiospecific Installation of Unsymmetrical Imine- Enamine and Imidazole Caps - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2014

Capping Methodology in Cyclodextrin Chemistry: Use of a Symmetrical Diketone Reagent for Regiospecific Installation of Unsymmetrical Imine- Enamine and Imidazole Caps

Résumé

Methylated - and -cyclodextrin skeletons were both equipped with an unsymmetrical N-(2-N-alkylaminoacenaphthenyl)alkylimine rigid handle. The capping reaction, which consists of condensing a diaminocyclodextrin with highly symmetrical acenaphthenequinone, was found to be regiospecific when starting from cyclodextrin-diamines without any symmetry element. All modified cyclooligosaccharides have intra-annular nitrogen donor atoms. They undergo further cyclization on oxidation, whether chemically with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone or electrochemically, to give highly strained cyclodextrins capped with an unsymmetrical 1,2-disubstituted 1H-imidazole unit.

Dates et versions

hal-01063267 , version 1 (11-09-2014)

Identifiants

Citer

Matthieu Jouffroy, Dominique Armspach, Alain Louati, Dominique Matt, Loic Toupet. Capping Methodology in Cyclodextrin Chemistry: Use of a Symmetrical Diketone Reagent for Regiospecific Installation of Unsymmetrical Imine- Enamine and Imidazole Caps. Chemistry - A European Journal, 2014, 20 (9), pp.2565-2573. ⟨10.1002/chem.201303556⟩. ⟨hal-01063267⟩
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