Chiral recognition inside a chiral cucurbituril

Angewandte Chemie - International Edition

Volumn 46, Issue 39, 2007, Pages 7425-7427

  Huang, Wei Hao ^a   Zavalij, Peter Y ^a   Isaacs, Lyle ^a  

^a University of Maryland   (United States)

Author keywords

Chirality; Cucurbiturils; Reaction mechanisms; Self assembly; Supramolecular chemistry

Indexed keywords

AMINO ACIDS; SELF ASSEMBLY; STEREOSELECTIVITY; SUPRAMOLECULAR CHEMISTRY;

CUCURBITURILS; REACTION MECHANISMS;

CHIRALITY;

EID: 35048843787     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200702189     Document Type: Article

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38. 2H) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
39. (±)-bis-ns-CB[6] features connections between two pairs of homotopic NH groups of identical topicity whereas previously isolated bis-ns-CB[10] has connections between two pairs of homotopic NH groups of opposite topicity.
40. The ROESY spectrum of the mixture of diastereomers did not provide information that would allow us to assign the major and minor resonances to a specific diastereomer. We are in the process of resolving this issue by separating the enantiomers of (±)-bis-ns-CB[6] by chromatography on a chiral stationary phase.
41. Compound 12 and (±)-bis-ns-CB[6] form a 1:1 inclusion complex rather than a supramolecular polymeric exclusion complex.
42. 2O under acidic conditions.
43. Several constitutional isomers of (±)-bis-ns-CB[n] are possible depending on the length of the glycoluril oligomer fragments that condense (e.g. (±)-bis-ns-CB[7] can be formed from tetramer and trimer fragments or from dimer and pentamer fragments).