Complete asymmetric induction of supramolecular chirality in a hydrogen-bonded assembly

Leonard J. Prins, Jurriaan Huskens, Feike de Jong, Peter Timmerman and David N. Reinhoudt ()
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Leonard J. Prins: Laboratory of Supramolecular Chemistry and Technology, MESA+ Research Institute, University of Twente
Jurriaan Huskens: Laboratory of Supramolecular Chemistry and Technology, MESA+ Research Institute, University of Twente
Feike de Jong: Laboratory of Supramolecular Chemistry and Technology, MESA+ Research Institute, University of Twente
Peter Timmerman: Laboratory of Supramolecular Chemistry and Technology, MESA+ Research Institute, University of Twente
David N. Reinhoudt: Laboratory of Supramolecular Chemistry and Technology, MESA+ Research Institute, University of Twente

Nature, 1999, vol. 398, issue 6727, 498-502

Abstract: Abstract Chirality at the supramolecular level involves the non-symmetric arrangement of molecular components in a non-covalent assembly1,2. Supramolecular chirality is abundant in biology, for example in the DNA double helix3, the triple helix of collagen4 and the α-helical coiled coil of myosin5. These structures are stabilized by inter-strand hydrogen bonds, and their handedness is determined by the configuration of chiral centres in the nucleotide or peptide backbone. Synthetic hydrogen-bonded assemblies have been reported that display supramolecular chirality in solution6,7,8 or in the solid state9,10,11,12. Complete asymmetric induction of supramolecular chirality—the formation of assemblies of a single handedness—has been widely studied in polymeric superstructures13,14. It has so far been achieved in inorganic metal-coordinated systems15,16,17, but not in organic hydrogen-bonded assemblies18,19,20. Here we describe the diastereoselective assembly of enantio-pure calix[4]arene dimelamines and 5,5-diethylbarbituric acid (DEB) into chiral hydrogen-bonded structures of one handedness. The system displays complete enantioselective self-resolution: the mixing of homomeric assemblies (composed of homochiral units) with opposite handedness does not lead to the formation of heteromeric assemblies. The non-covalent character of the chiral assemblies, the structural simplicity of the constituent building blocks and the ability to control the assembly process by means of peripheral chiral centres makes this system promising for the development of a wide range of homochiral supramolecular materials or enantioselective catalysts.

Date: 1999
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DOI: 10.1038/19053

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