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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Veröffentlicht in:Angewandte Chemie International Edition 2012-06, Vol.51 (26), p.6426-6431
Hauptverfasser: 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.
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container_end_page 6431
container_issue 26
container_start_page 6426
container_title Angewandte Chemie International Edition
container_volume 51
creator 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.
description 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.
doi_str_mv 10.1002/anie.201201701
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subjects Aggregates
deracemization
enantiomeric excess
Helical
Isomerism
Molecular Structure
nonlinear effects
Polymers - chemistry
Racemization
self-assembly
supramolecular chemistry
title Consequences of Cooperativity in Racemizing Supramolecular Systems
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