Angewandte Chemie International Edition 2012

An “Against the Rules” Double Bank Shot with Diisobutylaluminum Hydride To Allow Triple Functionalization of α-Cyclodextrin†

Dr. Elena Zaborova, Maxime Guitet, Dr. Giuseppe Prencipe, Prof. Yves Blériot (IC2MP), Dr. Mickaël Ménand, Prof. Matthieu Sollogoub

Article first published online: 22 NOV 2012

Keywords :

  • concave cycles;
  • cyclodextrin;
  • heterofunctionalization;
  • mechanistic studies;
  • selectivity

Angewandte_Chemie  02

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.

Angewandte Chemie International Edition

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