Enantioselective synthesis of rigid 2-aminotetralins. Utility of silicon as an oxygen and nitrogen surrogate in the tandem addition reaction

Journal of Organic Chemistry

Volumn 65, Issue 11, 2000, Pages 3503-3512

  Degnan, Andrew P ^a   Meyers, A I ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINOTETRALIN DERIVATIVE; NITROGEN; OXYGEN; SILICON;

ARTICLE; BINDING AFFINITY; CHIRALITY; MOLECULAR INTERACTION; OXIDATION; SYNTHESIS;

ANTIPARKINSON AGENTS; MAGNETIC RESONANCE SPECTROSCOPY; NITROGEN; OXYGEN; SILICON; STEREOISOMERISM; TETRAHYDRONAPHTHALENES;

EID: 0034595751     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0001131     Document Type: Article

References (35)

1. Cotzias, G. C.; Papavasiliou, P. S.; Fehling, C.; Kaufman, B.; Mena, I. New Engl. J. Med. 1970, 282, 31.
2. Vernier, V. G. Annu. Rep. Med. Chem. 1971, 1970, 42.
3. McDermed, J. D.; McKenzie, G. M.; Phillips, A. P. J. Med. Chem. 1975, 18, 362.
4. (a) Cannon, J. G.; Amoo, V. E. D.; Long, J. P.; Bhatnagar, R. K.; Flynn, J. R. J. Med. Chem. 1986, 29, 2529.
5. (b) Cannon, J. G.; Lee, T.; Goldman, H. D.; Long, J. P.; Flynn, J. R.; Verimer, T.; Costall, B.; Naylor, R. J. J. Med. Chem. 1980, 23, 1.
6. (c) Cannon, J. G.; Suarez-Gutierrez, C.; Lee, T.; Long, J. P.; Costall, B.; Fortune, D. H.; Naylor, R. J. J. Med. Chem. 1979, 22, 341.
7. For other syntheses of octahydrobenzo[f]quinolines, see: (a) Ripa, L.; Hallberg, A. J. Org. Chem. 1998, 63, 84. (b) Tagmatarchis, N.; Katerinopoulos, H. E. J. Heterocycl. Chem. 1996, 33, 983.
8. For other syntheses of octahydrobenzo[f]quinolines, see: (a) Ripa, L.; Hallberg, A. J. Org. Chem. 1998, 63, 84. (b) Tagmatarchis, N.; Katerinopoulos, H. E. J. Heterocycl. Chem. 1996, 33, 983.
9. (a) Wikström, H.; Andersson, B.; Elebring, T.; Svensson, K.; Carlsson, A.; Largent, B. J. Med. Chem. 1987, 30, 2169.
10. (b) Wikström, H.; Andersson, B.; Elebring, T.; Jacyno, J.; Allinger, N. L.; Svensson, K.; Carlsson, A.; Sundell, S. J. Med. Chem. 1987, 30, 1567.
11. (c) Wikström, H.; Sanchez, D.; Lindberg, P.; Arvidsson, L.-E.; Hacksell, U.; Johansson, A.; Nilsson, J. L. G.; Hjorth, S.; Carlsson, A. J. Med. Chem. 1982, 25, 925.
12. (a) Lin, C.-H.; Haadsma-Svensson, S. R.; Lahti, R. A.; McCall, R. B.; Piercey, M. F.; Schreur, P. D.; Von Voigtlander, P. F.; Smith, M. W.; Chidester, C. G. J. Med. Chem. 1993, 36, 1053.
13. (b) Cruse, S. F.; Lear, J.; Klein, C. L.; Andersen, P. H.; Dick, R. M.; Crider, A. M. J. Pharm. Sci. 1993, 82, 334.
14. Cannon, J. G. Prog. Drug Res. 1985, 29, 303.
15. (a) Hulme, A. N.; Meyers, A. I. J. Org. Chem. 1994, 59, 952.
16. (b) Hulme, A. N.; Henry, S. S.; Meyers, A. I. J. Org. Chem. 1995, 60, 1265.
17. For reviews on the use of chiral oxazolines in synthesis, see: (a) Meyers, A. I. J. Heterocycl. Chem. 1998, 35, 991. (b) Gant, T. G.; Meyers, A. I. Tetrahedron, 1994, 50, 2297. (c) Reuman, M.; Meyers, A. I. Tetrahedron 1985, 41, 837.
18. For reviews on the use of chiral oxazolines in synthesis, see: (a) Meyers, A. I. J. Heterocycl. Chem. 1998, 35, 991. (b) Gant, T. G.; Meyers, A. I. Tetrahedron, 1994, 50, 2297. (c) Reuman, M.; Meyers, A. I. Tetrahedron 1985, 41, 837.
19. For reviews on the use of chiral oxazolines in synthesis, see: (a) Meyers, A. I. J. Heterocycl. Chem. 1998, 35, 991. (b) Gant, T. G.; Meyers, A. I. Tetrahedron, 1994, 50, 2297. (c) Reuman, M.; Meyers, A. I. Tetrahedron 1985, 41, 837.
20. (a) Jones, G. R.; Landais, Y. Tetrahedron 1996, 52, 7599.
21. (b) Fleming, I.; Henning, R.; Plaut, H. J. Chem. Soc., Chem. Commun. 1984, 29.
22. (c) Tamao, K.; Kakui, T.; Akita, M.; Iwahara, T.; Kanatani, R.; Yoshida, J.; Kumada, M. Tetrahedron 1983, 39, 990.
23. For an earlier report of a naphthyloxazoline-based sythesis of 2-aminotetralins, see: Shimano, M.; Meyers, A. I. J. Org. Chem. 1995, 60, 7445.
24. 1H NMR.
25. Henry, L. C. R. Hebd. Seances Acad. Sci. 1895, 120, 1265.
26. Ochiai, M.; Arimoto, M.; Fujita, E. Tetrahedron Lett. 1980, 4557.
27. Meyers, A. I.; Sircar, J. C. J. Org. Chem. 1967, 32, 4134.
28. Shvekhgeimer, M.-G. A. Russ. Chem. Rev. 1998, 67, 35.
29. (a) Zschiesche, R.; Reissig, H.-U. Tetrahedron Lett. 1988, 29, 1685.
30. (b) Zschiesche, R. Liebigs Ann. Chem. 1989, 551.
31. Sar, C. P.; Kalai, T.; Baracz, N. M.; Jerkovich, G.; Hideg, K. Synth. Commun. 1995, 25, 2929.
32. For other syntheses of pyrrolidines and piperidines using a double reductive animation, see: (a) Barili, P. L.; Berti, G.; Catelani, G.; D'Andrea, F.; De Rensis, F.; Puccioni, L. Tetrahedron 1997, 53, 3407. (b) Solé, D.; Bosch, J.; Bonjoch, J. Tetrahdron 1996, 52, 4013. (c) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175 and references therein.
33. For other syntheses of pyrrolidines and piperidines using a double reductive animation, see: (a) Barili, P. L.; Berti, G.; Catelani, G.; D'Andrea, F.; De Rensis, F.; Puccioni, L. Tetrahedron 1997, 53, 3407. (b) Solé, D.; Bosch, J.; Bonjoch, J. Tetrahdron 1996, 52, 4013. (c) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175 and references therein.
34. For other syntheses of pyrrolidines and piperidines using a double reductive animation, see: (a) Barili, P. L.; Berti, G.; Catelani, G.; D'Andrea, F.; De Rensis, F.; Puccioni, L. Tetrahedron 1997, 53, 3407. (b) Solé, D.; Bosch, J.; Bonjoch, J. Tetrahdron 1996, 52, 4013. (c) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175 and references therein.
35. For a review of phosphorous-based olefinations, see: Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863.