A new approach to A,B-difunctionalisation of cyclodextrins using bulky 1,3-bis[bis(aryl)chloromethyl]benzenes as capping reagents

Abstract

1,3-Bis[bis(4-tert-butylphenyl)chloromethyl]benzene and 1,3-bis[bis(4-anisyl)chloromethyl]benzene were employed as regioselective capping reagents for the preparation of C-6^A,C-6^B-bridged, permethylated α- and β-CD derivatives; isolated yields up to 55% of proximally capped, methylated CDs were obtained, thus opening the way to the straightforward preparation of a wide range of A,B-functionalised CDs. As revealed by a single crystal X-ray diffraction study, the benzene-1,3-bis[bis(4-tert-butylphenyl)methyl] spacer is perfectly suited for A,B-capping of β-cyclodextrin.