title: Chemospecific monofunctionalization of alpha-cyclodextrin in the solid state
abstract: [reaction: see text] The properties of the self-assembling aziadamantane inclusion complex with two alpha-cyclodextrin molecules have been exploited to perform a chemospecific monofunctionalization of alpha-cyclodextrin. The insertion of the photochemically generated carbenes takes place chemospecifically into the cyclodextrin's C-3-OH and C-2-OH bonds in 39 and 18% yield, respectively. This model reaction surpasses conventional methods in terms of yield as well as selectivity.
authors.affiliation: Institut fur Organische Chemie der Universitat Wien, Austria.
authors.initials: D
authors.lastname: Krois
authors.initials: MM
authors.lastname: Bobek
authors.initials: A
authors.lastname: Werner
authors.initials: H
authors.lastname: Kahlig
authors.initials: UH
authors.lastname: Brinker