Convenient synthesis of mono(6A-N-allylamino-6A-deoxy)permethylated β-cyclodextrin: a promising chiral selector for an HPLC chiral stationary phase

Mono(6-(p-toluenesulfonyl))permethylated β-cyclodextrin, a versatile precursor for a wide variety of mono-functionalized permethyl β-cyclodextrins, has been generated successfully by the direct methylation of monotosylated cyclodextrin. This afforded a convenient synthesis of mono(6A-N-allylamino-6A-deoxy)permethylated β-cyclodextrin. Hydrosilylation of the chiral selector with (EtO)3SiH and reaction of the resultant reactive siloxane with pristine silica gel afforded a facile entry into a structurally well-defined chiral HPLC stationary phase.