Enantiomerically enriched vic-amino alcohols from 2-iminobornanes

Tetrahedron Asymmetry

Volumn 13, Issue 17, 2002, Pages 1849-1854

  Squire, Michael D ^a   Burwell, Amanda ^a   Ferrence, Gregory M ^a   Hitchcock, Shawn R ^a  

^a ILLINOIS STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 PHENYL 2 (1,7,7 TRIMETHYLBICYCLO[2.2.1]HEPT 2 YLIDENEAMINO)PROPAN 1 OL; 2 (1,7,7 TRIMETHYLBICYCLO[2.2.1]HEPT 2 YLIDENEAMINO)ETHANOL; 2 PHENYL 2 (1,7,7 TRIMETHYLBICYCLO[2.2.1]HEPT 2 YLIDENEAMINO)ETHANOL; ALCOHOL DERIVATIVE; ALUMINUM DERIVATIVE; AMINE; BORNANE DERIVATIVE; CAMPHOR DERIVATIVE; ETHANOLAMINE; IMINE; NOREPHEDRINE; PHENYLGLYCINOL; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COLUMN CHROMATOGRAPHY; DRUG SYNTHESIS; ENANTIOMER; POLYMERIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; X RAY CRYSTALLOGRAPHY;

EID: 0037048293     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00486-X     Document Type: Article

References (42)

1. 'Chiral Pharmaceuticals': Stinson S.C. Chem. Eng. News. 79:2001;79-97.
2. Delogu G., Fabbri D., de Candia C., Patti A., Pedotti S. Tetrahedron: Asymmetry. 13:2002;891.
3. Zhou H., Lu S., Xie R., Chan A.S.C., Yang T.-K. Tetrahedron Lett. 42:2001;1107.
4. Santhi V., Rao J.M. Synth. Commun. 30:2000;4329.
5. Altava B., Burguete M.I., García Verdugo E., Luis S.V., Pozo O., Salvador R.V. Eur. J. Org. Chem. 1999;2263.
6. Reiners I., Wilken J., Martens J. Tetrahedron: Asymmetry. 6:1995;3063 Kim, H. Y.; Park, D. H.; B., I. S.; Yoon, I. K.; Park, C. S. J. Org. Chem. 1993, 58, 4511.
7. Kim, H. Y.; Park, D. H.; B., I. S.; Yoon, I. K.; Park, C. S. J. Org. Chem. 1993, 58, 4511.
8. García Martinez A., Teso Vilar E., García Fraile A., de la Moya Cerero S., Martínez-Ruiz P., Chicharro Villas P. Tetrahedron: Asymmetry. 13:2002;1.
9. Dimitrov V., Dobrikov G., Genov M. Tetrahedron: Asymmetry. 12:2001;1323.
10. Orsini F., Sello G., Bestetti G. Tetrahedron: Asymmetry. 12:2001;2961.
11. García Martinez A., Teso Vilar E., García Fraile A., de la Moya Cerero S., Martínez-Ruiz P. Tetrahedron: Asymmetry. 9:1998;1737.
12. Przeslawski R.M., Newman S., Thornton E.R., Joullie M.M. Synth. Commun. 25:1995;2975.
13. Noyori R., Kitamura M. Angew. Chem., Int. Ed. Engl. 30:1991;49.
14. Kouklovsky C., Pouihes A., Langlois Y. J. Am. Chem. Soc. 112:1990;6672.
15. Seyden-Penne J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis. 1995;John Wiley & Sons, New York.
16. Koskinen A. Asymmetric Synthesis of Natural Products. 1993;John Wiley & Sons, New York.
17. Hitchcock S.R., Nora G.P., Casper D.M., Squire M.D., Maroules C.D., Ferrence G.M., Szczepura L.F., Standard J.M. Tetrahedron. 57:2001;9789.
18. Hitchcock S.R., Casper D.M., . Nora G.P., Blackburn J.R., Bentley J.T., Taylor D.C. J. Heterocycl. Chem. 39:2002;823.
19. Page P.C.B., Murrell V.L., Limousin C., Laffan D.D.P., Bethell D., Slawin A.M.Z., Smith T.A.D. J. Org. Chem. 65:2000;4204.
20. Morris D.G., Ryder K.S. Synthesis. 1997;620.
21. Guziec F.S. Jr., Russo J.M. Synthesis. 1984;479.
22. Bondavalli F., Schenone P., Ranise A. Synthesis. 1979;830.
23. D=-31.7 (c 0.76, 1N HCl) from Aldrich Chemical Co.
24. D=-31.7 (c 0.76, 1N HCl) from Aldrich Chemical Co.
25. D=-31.7 (c 0.76, 1N HCl) from Aldrich Chemical Co.
26. For examples of (R)-(-)-phenylglycinol as a chiral auxiliary, see: (a) Meyers, A. I.; Downing, S. V.; Weiser, M. J. J. Org. Chem. 2001, 66, 1413; (b) Santes, V.; Gómez, E.; Zárate, V.; Santillan, R.; Farfán, N.; Rojas-Lima, S. Tetrahedron: Asymmetry 2001, 12, 241; (c) Roussi, F.; Bonin, M.; Chiaroni, A.; Micouin, L.; Riche, C.; Husson, H.-P. Tetrahedron Lett. 1998, 39, 8081.
27. For examples of (R)-(-)-phenylglycinol as a chiral auxiliary, see: (a) Meyers, A. I.; Downing, S. V.; Weiser, M. J. J. Org. Chem. 2001, 66, 1413; (b) Santes, V.; Gómez, E.; Zárate, V.; Santillan, R.; Farfán, N.; Rojas-Lima, S. Tetrahedron: Asymmetry 2001, 12, 241; (c) Roussi, F.; Bonin, M.; Chiaroni, A.; Micouin, L.; Riche, C.; Husson, H.-P. Tetrahedron Lett. 1998, 39, 8081.
28. For examples of (R)-(-)-phenylglycinol as a chiral auxiliary, see: (a) Meyers, A. I.; Downing, S. V.; Weiser, M. J. J. Org. Chem. 2001, 66, 1413; (b) Santes, V.; Gómez, E.; Zárate, V.; Santillan, R.; Farfán, N.; Rojas-Lima, S. Tetrahedron: Asymmetry 2001, 12, 241; (c) Roussi, F.; Bonin, M.; Chiaroni, A.; Micouin, L.; Riche, C.; Husson, H.-P. Tetrahedron Lett. 1998, 39, 8081.
29. 1H NMR spectra.
30. 2 or fail to yield any product in significant amounts.
31. Love B.E., Ren J. J. Org. Chem. 58:1993;5556.
32. Cerreta F., Leriverend C., Metzner P. Tetrahedron Lett. 34:1993;6741.
33. Caution: Many N-nitrosamines are known to have carcinogenic activity. See: (a) Nitrosamines and Related N-Nitroso Compounds: Chemistry and Biochemistry; Loeppky, R. N.; Michejda, C. J., Eds.; ACS Symposium Series 553, 1994; (b) Linjinsky, W.; Reuber, M. D.; Saavedra, J. E.; Singer, G. M. J. Natl. Cancer Inst. 1983, 70, 959.
34. Caution: Many N-nitrosamines are known to have carcinogenic activity. See: (a) Nitrosamines and Related N-Nitroso Compounds: Chemistry and Biochemistry; Loeppky, R. N.; Michejda, C. J., Eds.; ACS Symposium Series 553, 1994; (b) Linjinsky, W.; Reuber, M. D.; Saavedra, J. E.; Singer, G. M. J. Natl. Cancer Inst. 1983, 70, 959.
35. Crystallographic data (excluding structure factors) for structure 12 reported in this paper have been deposited with the Cambridge Crystallographic Data Centre. The atomic coordinates and equivalent isotropic displacement coefficients are included in the deposited material (CCDC 190337) as are a complete list of bond distances and angles. Copies of available material can be obtained, free of charge, on application to the CCDC, 12 Union Road, Cambridge CB2, 1EZ, UK (Fax:+44-1223-336033 or e-mail: deposit@ccdc.am.ac.uk).
36. Enraf-Nonius, CAD4 Express Software, Delft, The Netherlands, 1994.
37. Harms, K.; Wocadlo, S. XCAD-4: Program for Processing CAD-4 Diffractometer Data, University of Marburg, Germany, 1995.
38. McArdle P. J. Appl. Crystallogr. 29:1996;306.
39. North A.C.T., Phillips D.C., Mathews F.S. Acta Crystallogr. A24:1968;351.
40. Farrugia L.J. J. Appl. Crystallogr. 32:1999;837.
41. (a) Altomare A., Cascarano G., Giacovazzo C., Guagliardi A. J. Appl. Crystallogr. 26:1993;343
42. (b) Sheldrick, G. M. SHELX-97: Programs for Crystal Structure Analysis (Release 97-2), University of Göttingen, Germany, 1997.