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. 2013 Jan 7;52(2):639-44.
doi: 10.1002/anie.201204974. Epub 2012 Nov 22.

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

Elena Zaborova  1 , Maxime Guitet, Giuseppe Prencipe, Yves Blériot, Mickaël Ménand, Matthieu Sollogoub
Affiliations

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

Elena Zaborova et al. Angew Chem Int Ed Engl. .

Abstract

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.

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