Chiral discrimination in hydrogen-bonded [7]helicenes

Organic Letters

Volumn 2, Issue 20, 2000, Pages 3169-3172

  Murguly, Elisa ^a   McDonald, Robert ^a   Branda, Neil R ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000492788     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006366y     Document Type: Article

References (23)

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12. For other studies that use rigid polyazaclefts, helicopodands, or bifunctional helicenes for hydrogen-bonding recognition, see: (a) Perreault, D. M.; Chen, X.; Anslyn, E. V. Tetrahedron 1995, 51, 353.
13. (b) Huang, C.-Y.; Lynch, V.; Anslyn, E. V. Angew. Chem., Int. Ed. Engl. 1992, 31, 1244.
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18. For a description of M and P nomenclature and how it is used to describe the stereochemistry of helicenes, see: Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1994; Chapter 14, pp 1121, 1163-1166.
19. The precursor to 2b was prepared as described for the methyl ether: Osborne, A. G.; Miller, L. A. D. J. Chem. Soc., Perkin Trans, 1 1993, 181.
20. 13C NMR spectroscopy, infrared spectroscopy, and mass spectrometry.
21. 1H NMR of 4a (R = H) shows a resonance peak at 9.22 ppm, characteristic of the S-isomer. Katz, T. J.; Sudhakar, A.; Teasley, M. F.; Gilbert, A. M.; Geiger, W. E.; Robben, M. P.; Wuensch, M.; Ward, M. D. J. Am. Chem. Soc. 1993, 115, 3182.
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23. Navaza, J.; Toucaris, G.; Le Bas, G.; Navaza, A.; de Rango, C. Bull. Soc. Chim. Belg. 1979, 88, 863.