Enantioselective cyclization of racemic supramolecular polymers

A.T. Cate, ten; P.Y.W. Dankers; H. Kooijman; A.L. Spek; R.P. Sijbesma; E.W. Meijer

doi:10.1021/ja034273g

Enantioselective cyclization of racemic supramolecular polymers

A.T. Cate, ten, P.Y.W. Dankers, H. Kooijman, A.L. Spek, R.P. Sijbesma, E.W. Meijer

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Abstract

Homochiral hydrogen-bonded cyclic assemblies are formed in dilute solutions of racemic supramolecular polymers based on the quadruple hydrogen bonding 2-ureido-4[1H]-pyrimidinone unit, as observed by 1H NMR and SEC experiments. Preorganization of the monomers and the combined binding strength of the eight hydrogen bonds result in a very high stability of the cyclic aggregates with pronounced selectivity between homochiral and heterochiral cyclic species, usually only observed in crystalline or liquid crystalline phases.

Original language	English
Pages (from-to)	6860-6861
Number of pages	1
Journal	Journal of the American Chemical Society
Volume	125
Issue number	23
DOIs	https://doi.org/10.1021/ja034273g
Publication status	Published - 2003

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abstract = "Homochiral hydrogen-bonded cyclic assemblies are formed in dilute solutions of racemic supramolecular polymers based on the quadruple hydrogen bonding 2-ureido-4[1H]-pyrimidinone unit, as observed by 1H NMR and SEC experiments. Preorganization of the monomers and the combined binding strength of the eight hydrogen bonds result in a very high stability of the cyclic aggregates with pronounced selectivity between homochiral and heterochiral cyclic species, usually only observed in crystalline or liquid crystalline phases.",

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AU - Cate, ten, A.T.

AU - Dankers, P.Y.W.

AU - Kooijman, H.

AU - Spek, A.L.

AU - Sijbesma, R.P.

AU - Meijer, E.W.

PY - 2003

Y1 - 2003

N2 - Homochiral hydrogen-bonded cyclic assemblies are formed in dilute solutions of racemic supramolecular polymers based on the quadruple hydrogen bonding 2-ureido-4[1H]-pyrimidinone unit, as observed by 1H NMR and SEC experiments. Preorganization of the monomers and the combined binding strength of the eight hydrogen bonds result in a very high stability of the cyclic aggregates with pronounced selectivity between homochiral and heterochiral cyclic species, usually only observed in crystalline or liquid crystalline phases.

AB - Homochiral hydrogen-bonded cyclic assemblies are formed in dilute solutions of racemic supramolecular polymers based on the quadruple hydrogen bonding 2-ureido-4[1H]-pyrimidinone unit, as observed by 1H NMR and SEC experiments. Preorganization of the monomers and the combined binding strength of the eight hydrogen bonds result in a very high stability of the cyclic aggregates with pronounced selectivity between homochiral and heterochiral cyclic species, usually only observed in crystalline or liquid crystalline phases.

U2 - 10.1021/ja034273g

DO - 10.1021/ja034273g

M3 - Article

C2 - 12783526

SN - 0002-7863

VL - 125

SP - 6860

EP - 6861

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 23

ER -

Enantioselective cyclization of racemic supramolecular polymers

Abstract

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