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108. Covalent capture of dynamic hydrogen-bonded assemblies

Author

Cardullo, F., primary, Calama, M. Crego, additional, Snellink-Ruël, B. H. M., additional, Weidmann, J.-L., additional, Bielejewska, A., additional, Timmerman, P., additional, Reinhoudt, D. N., additional, Fokkens, R., additional, and Nibbering, N. M. M., additional

Published
2000
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113. Diastereoselective Noncovalent Synthesis of Hydrogen-Bonded Double-Rosette Assemblies

Author

Prins, LEONARD JAN, Hulst, R., Timmerman, P., and Reinhoudt, D. N.

Subjects
Self-Assembly, Diastereoselectivity, Noncovalent interactions, Organic Chemistry, Supramolecular chirality, General Chemistry, Catalysis, Hydrogen bonds
Abstract

Chiral centers present either in the dimelamine components of calix[4]arene 1 or in the cyanurate components CA quantitatively induce one handedness (P or M) in the corresponding hydrogen-bonded assemblies 13(CA)6 (de>98 %). The high degree of chiral induction results from the presence of six chiral centers in close proximity (Cα) to the core of the assembly. A much lower level of chiral induction is observed for assemblies with chiral centers that are more remote (Cβ). All diastereomerically pure assemblies 13(CA)6 exhibit very high CD activities (|Δεmax|100 L mol-1 cm-1), in sharp contrast to the low CD activities (|Δεmax|8 L mol-1 cm-1) shown by the free components. The assemblies display spontaneous resolution under thermodynamically controlled conditions (i.e., heteromeric assemblies containing both peripheral R and S centers are not observed. Remarkable assembly behavior is observed if both components 1 and CA are chiral. In general, formation of well-defined assemblies is only observed when both components contain unidirectional information for the induction of either M or P chirality.

Published
2002
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