An efficient strategy for the modification of α-cyclodextrin: direct conversion of one or two adjacent 6-OHs to phthalimides

α-Cyclodextrin was reacted with phthalimide under modified Mitsunobu conditions to give the 6A-deoxy-6A-phthalimido-α-cyclodextrin in 41% yield. This reaction also worked well in the modification of two methylene carbons, giving the 6A,6B-, 6A,6C- and 6A,6D-diphthalimido-α-cyclodextrins in 22, 9.5 and 4.6% isolated yields, respectively. All the phthalimido species can be quantitatively converted to the corresponding amino cyclodextrins by hydrazinolysis.