Use of the olefin metathesis reaction for highly efficient b-cyclodextrin modification

A series of novel primary face mono-substituted β-cyclodextrin derivatives have been synthesised using the olefin metathesis reaction. Mono-6-allylamino-6-deoxy-β-cyclodextrin easily synthesised by nucleophilic substitution of mono-6-tosyl-β-cyclodextrin is the key synthon in the preparation of cyclodextrin derivatives mono-functionalised at the primary face by alkyl, aryl or perfluoroalkyl groups using Grubbs catalyst. In the cases of vinylbenzene and 1H,1H,2H-perfluoro-1-octene, the metathesis reactions yield with 95% stereoselectivity of the E -isomer.