Regiospecific Tandem Azide-Reduction/Deprotection To Afford Versatile Amino Alcohol-Functionalized α- and β-Cyclodextrins


  • We thank Dr. P. Pelupessy and Prof. G. Bodenhausen for 600 MHz NMR analysis, Ophélie Kwasnieski for assistance with molecular modeling studies, Prof. D. Curran for proofreading the manuscript, and Cyclolab for generously supplying cyclodextrins.


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Cyclic conundrum: Deciphering the cyclic directionality of cyclodextrins allows the precise regiospecific synthesis of functionalized cyclodextrins with diametrically opposed amino and hydroxy groups (see scheme; DIBAL-H=diisobutylaluminum hydride, Bn=benzyl) through a tandem azide-reduction/debenzylation mechanism. A remarkable feature of this process is the long-distance discrimination between two equidistant benzyl groups on β-cyclodextrin.