A facile route into 6(A)-mono-ω-alkenylcarbamido-6(A)-deoxy- perfunctionalised cyclodextrin: Key intermediate for further reactive functionalisations

Abstract

The Staudinger reaction was applied to the facile synthetic generation of a series of mono-6-alkylcarbamido-6-deoxy-perfunctionalised cyclodextrins and mono-6-ω-alkenylcarbamido-6-deoxy-perfunctionalised cyclodextrins. The latter compound with ω-alkenyl pendants was shown to be amenable to further reactive transformations as exemplified by a facile hydrosilylation with (RO)3SiH in the presence of platinum catalysts to afford reactive siloxane intermediates which can be immobilised onto silica gel for application as an efficient chiral stationary phase for enantioseparation applications.