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

Elena Zaborova; Maxime Guitet; Giuseppe Prencipe; Yves Blériot; Mickaël Ménand; Matthieu Sollogoub

doi:10.1002/anie.201204974

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

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

Authors

Elena Zaborova¹, Maxime Guitet, Giuseppe Prencipe, Yves Blériot, Mickaël Ménand, Matthieu Sollogoub

Affiliation

¹ UPMC Univ Paris, Institut Universitaire de France, Institut Parisien de Chimie Moléculaire, UMR-CNRS, France.

PMID: 23172810
DOI: 10.1002/anie.201204974

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.

MeSH terms

Models, Molecular
Organometallic Compounds / chemistry*
Stereoisomerism
alpha-Cyclodextrins / chemistry*

Substances

Organometallic Compounds
alpha-Cyclodextrins
diisobutylaluminum
alpha-cyclodextrin