Consequences of Cooperativity in Racemizing Supramolecular Systems

Saluting the sergeant: Phg‐BTA (see scheme) cooperatively self‐assembles into helical aggregates and shows unprecedented racemization behavior in the presence of base. In thermodynamically controlled conditions, the addition of a small amount of chiral auxiliary to this mixture results in a deracemi...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2012-06, Vol.51 (26), p.6426-6431
Main Authors: Cantekin, Seda, ten Eikelder, Huub M. M., Markvoort, Albert J., Veld, Martijn A. J., Korevaar, Peter A., Green, Mark M., Palmans, Anja R. A., Meijer, E. W.
Format: Article
Language:English
Subjects:
Aggregates
deracemization
enantiomeric excess
Helical
Isomerism
Molecular Structure
nonlinear effects
Polymers - chemistry
Racemization
self-assembly
supramolecular chemistry
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Summary:Saluting the sergeant: Phg‐BTA (see scheme) cooperatively self‐assembles into helical aggregates and shows unprecedented racemization behavior in the presence of base. In thermodynamically controlled conditions, the addition of a small amount of chiral auxiliary to this mixture results in a deracemization reaction and a final enantiomeric excess of 32 %. A theoretical model is presented to understand in detail the results obtained.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201201701