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.
Related Concept Videos
Prochirality
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Cycloaddition Reactions: MO Requirements for Thermal Activation
Ion Exchange


