Consequences of cooperativity in racemizing supramolecular systems

Seda Cantekin; Huub M.M. Ten Eikelder; Albert J. Markvoort; Martijn A.J. Veld; Peter A. Korevaar; Mark M. Green; Anja R.A. Palmans; E. W. Meijer

doi:10.1002/anie.201201701

Consequences of cooperativity in racemizing supramolecular systems

Seda Cantekin, Huub M.M. Ten Eikelder, Albert J. Markvoort, Martijn A.J. Veld, Peter A. Korevaar, Mark M. Green, Anja R.A. Palmans, E. W. Meijer

Chemical and Biomolecular Engineering

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English (US)
Pages (from-to)	6426-6431
Number of pages	6
Journal	Angewandte Chemie - International Edition
Volume	51
Issue number	26
DOIs	https://doi.org/10.1002/anie.201201701
State	Published - Jun 25 2012

Keywords

deracemization
enantiomeric excess
nonlinear effects
self-assembly
supramolecular chemistry

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.201201701

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title = "Consequences of cooperativity in racemizing supramolecular systems",

abstract = "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.",

keywords = "deracemization, enantiomeric excess, nonlinear effects, self-assembly, supramolecular chemistry",

author = "Seda Cantekin and {Ten Eikelder}, {Huub M.M.} and Markvoort, {Albert J.} and Veld, {Martijn A.J.} and Korevaar, {Peter A.} and Green, {Mark M.} and Palmans, {Anja R.A.} and Meijer, {E. W.}",

year = "2012",

month = jun,

day = "25",

doi = "10.1002/anie.201201701",

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volume = "51",

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journal = "Angewandte Chemie - International Edition",

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T1 - Consequences of cooperativity in racemizing supramolecular systems

AU - Cantekin, Seda

AU - Ten Eikelder, Huub M.M.

AU - Markvoort, Albert J.

AU - Veld, Martijn A.J.

AU - Korevaar, Peter A.

AU - Green, Mark M.

AU - Palmans, Anja R.A.

AU - Meijer, E. W.

PY - 2012/6/25

Y1 - 2012/6/25

N2 - 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.

AB - 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.

KW - deracemization

KW - enantiomeric excess

KW - nonlinear effects

KW - self-assembly

KW - supramolecular chemistry

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 26

ER -

Consequences of cooperativity in racemizing supramolecular systems

Abstract

Keywords

ASJC Scopus subject areas

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