Adsorption-induced asymmetric transformation of planar-chiral pyridinophanes

Tetrahedron Letters

Volumn 44, Issue 18, 2003, Pages 3625-3628

  Kanomata, Nobuhiro ^a   Oikawa, Jun ^a  

^a MEIJI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADSORBENT; ALUMINUM OXIDE; BRIDGED COMPOUND; CYCLOPHANE DERIVATIVE; NICOTINAMIDE DERIVATIVE; PYRIDINOPHANE DERIVATIVE; UNCLASSIFIED DRUG;

ADSORPTION; ARTICLE; CHIRALITY; CRYSTALLIZATION; POROSITY; SOLID; STEREOCHEMISTRY;

EID: 0037471455     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00699-3     Document Type: Article

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18. For recent papers on CIAT, see: (a) Komatsu, H.; Awano, H. J. Org. Chem. 2002, 67, 5419-5421; (b) Cimarelli, C.; Mazzanti, A.; Palmieri, G.; Volpini, E. J. Org. Chem. 2001, 66, 4759-4765; (c) Ates, A.; Curran, D. P. J. Am. Chem. Soc. 2001, 123, 5130-5131; (d) Boesten, W. H. J.; Seerden, J.-P. G.; Lange, B. d.; Dielemans, H. J. A.; Elsenberg, H. L. M.; Kaptein, B.; Moody, H. M.; Kellogg, R. M.; Broxterman, Q. B. Org. Lett. 2001, 3, 1121-1124; (e) Silverberg, L. J.; Kelly, S.; Vemishetti, P.; Vipond, D. H.; Gibson, F. S.; Harrison, B.; Spector, R.; Dillon, J. L. Org. Lett. 2000, 2, 3281-3283; (f) Node, M.; Nishide, K.; Fujiwara, T.; Ichihashi, S. Chem. Commun. 1998, 2363-2364.
19. For recent papers on CIAT, see: (a) Komatsu, H.; Awano, H. J. Org. Chem. 2002, 67, 5419-5421; (b) Cimarelli, C.; Mazzanti, A.; Palmieri, G.; Volpini, E. J. Org. Chem. 2001, 66, 4759-4765; (c) Ates, A.; Curran, D. P. J. Am. Chem. Soc. 2001, 123, 5130-5131; (d) Boesten, W. H. J.; Seerden, J.-P. G.; Lange, B. d.; Dielemans, H. J. A.; Elsenberg, H. L. M.; Kaptein, B.; Moody, H. M.; Kellogg, R. M.; Broxterman, Q. B. Org. Lett. 2001, 3, 1121-1124; (e) Silverberg, L. J.; Kelly, S.; Vemishetti, P.; Vipond, D. H.; Gibson, F. S.; Harrison, B.; Spector, R.; Dillon, J. L. Org. Lett. 2000, 2, 3281-3283; (f) Node, M.; Nishide, K.; Fujiwara, T.; Ichihashi, S. Chem. Commun. 1998, 2363-2364.
20. For recent papers on CIAT, see: (a) Komatsu, H.; Awano, H. J. Org. Chem. 2002, 67, 5419-5421; (b) Cimarelli, C.; Mazzanti, A.; Palmieri, G.; Volpini, E. J. Org. Chem. 2001, 66, 4759-4765; (c) Ates, A.; Curran, D. P. J. Am. Chem. Soc. 2001, 123, 5130-5131; (d) Boesten, W. H. J.; Seerden, J.-P. G.; Lange, B. d.; Dielemans, H. J. A.; Elsenberg, H. L. M.; Kaptein, B.; Moody, H. M.; Kellogg, R. M.; Broxterman, Q. B. Org. Lett. 2001, 3, 1121-1124; (e) Silverberg, L. J.; Kelly, S.; Vemishetti, P.; Vipond, D. H.; Gibson, F. S.; Harrison, B.; Spector, R.; Dillon, J. L. Org. Lett. 2000, 2, 3281-3283; (f) Node, M.; Nishide, K.; Fujiwara, T.; Ichihashi, S. Chem. Commun. 1998, 2363-2364.
21. Pyridinophane derivatives were recovered in 98% yield by desorption with ethanol after being left on silica gel at room temperature for a month.
22. Crystal structure data for (S,3′S)-1a are available on request from the Director of Cambridge Crystallographic Data Center (CDCC), 12 Union Road, Cambridge CB2 1EZ, UK.