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An “Against the Rules” Double Bank Shot with Diisobutylaluminum Hydride To Allow Triple Functionalization of α‐Cyclodextrin
Author(s) -
Zaborova Elena,
Guitet Maxime,
Prencipe Giuseppe,
Blériot Yves,
Ménand Mickaël,
Sollogoub Matthieu
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201204974
Subject(s) - regioselectivity , frustration , cyclodextrin , hydride , surface modification , chemistry , combinatorial chemistry , psychology , catalysis , organic chemistry , social psychology , hydrogen
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.