Diastereoselective noncovalent synthesis of hydrogen-bonded double-rosette assemblies

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Prins, Leonard J. and Hulst, Ron and Timmerman, Peter and Reinhoudt, David N. (2002) Diastereoselective noncovalent synthesis of hydrogen-bonded double-rosette assemblies. Chemistry: a European journal, 8 (10). pp. 2288-2301. ISSN 0947-6539

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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.
Item Type:Article
Additional information:686
Copyright:© 2002 WILEY-VCH Verlag
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Link to this item:http://purl.utwente.nl/publications/37949
Official URL:http://dx.doi.org/10.1002/1521-3765(20020517)8:10<2288::AID-CHEM2288>3.0.CO;2-3
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