An "against the rules" double bank shot with diisobutylaluminum hydride to allow triple functionalization of α-cyclodextrin.


Frustration leads to overreaction: when diametrically opposed regioselective debenzylation is frustrated, an unexpected double debenzylation reaction affords original tetrafunctionalized cyclodextrins in a controlled and efficient manner. A rationale of the reaction is proposed based on a kinetic study. 
DOI: 10.1002/anie.201204974


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