Chemospecific monofunctionalization of alpha-cyclodextrin in the solid state
[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.
Krois
D
Institut fur Organische Chemie der Universitat Wien, Austria.
Bobek
MM
Werner
A
Kahlig
H
Brinker
UH