An efficient synthesis of optically pure (S)-2-functionalized 1,2,3,4-tetrahydroquinoline

Tetrahedron Letters

Volumn 45, Issue 5, 2004, Pages 1027-1029

  Ding, Ke ^a   Flippen Anderson, Judy ^b,c   Deschamps, Jeffrey R ^b   Wang, Shaomeng ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

^b NAVAL RESEARCH LABORATORY   (United States)

^c RUTGERS UNIVERSITY   (United States)

Author keywords

Copper; Optically pure; Swern oxidation; Synthesis; Tetrahydroquinoline

Indexed keywords

1,2,3,4 TETRAHYDROQUINOLINE DERIVATIVE; 2 HYDROXYMETHYL 1,2,3,4 TETRAHYDROQUINOLINE; AMINO ACID; COPPER; HALIDE; PROPYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; SPECTRUM; SWERN OXIDATION;

EID: 0346392191     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.11.086     Document Type: Article

References (18)

1. Leeson P.D., Carling R.W., Moore K.W., Mosely A.M., Smith J.D., Stevenson G., Chan T., Baker R., Foster A.C., Grimwood S., Kemp J.A., Marshell G.R., Hoogsteen K. J. Med. Chem. 35:1992;1954-1968.
2. Nagata R., Tanno N., Kodo T., Ae N., Yamaguchi H., Tamiki N., Antoku F., Tatsuno T., Kato T., Tanaka Y., Nakamura M. J. Med. Chem. 37:1994;3956-3968.
3. Guo F., Chang B.H., Rizzo C.J. Bio. Med. Chem. Lett. 12:2002;151-154.
4. Nagata, R.; Tanno, N.; Kodo, T. PCT Int. Appl., WO 9308188, 1993.
5. Ejima, A.; Ohsuki, S.; Ohki, H.; Naito, H. U.S. 6,169,086.
6. Stanton J.L., Ackerman M.H. J. Med. Chem. 26:1983;986-989.
7. Kojima, K.; Aizawa, Y.; Samata, N.; Sakai, J.; Koyama, K.; Tonohiro, T.; Sugimoto, M.; Hara, T.; Hisamoto, M.; Homma, H. PCT Int. Appl., WO 9623789, 1996.
8. Katritsky A.R., Rachwal S., Rachwal B. Tetrahedron. 52:1996;15031-15070. and references cited therein.
9. Gallou-Dagommer I., Gastaud P., Rajanbabu T.V. Org. Lett. 3:2001;2053-2056. and references cited therein.
10. Ma D., Xia C., Jiang J., Zhang J., Tang W. J. Org. Chem. 68:2003;10442-10451.
11. Ma D., Xia C., Jiang J., Zhang J. Org. Lett. 3:2001;2189.
12. Fabio R.D., Alvaro G., Bertani B., Donati D., Giacobe S., Marchioro C., Palma C., Lynn S.M. J. Org. Chem. 67:2002;7319-7328.
13. Varady J., Wu X., Fang X., Min J., Hu Z., Levant B., Wang S. J. Med. Chem. 46:2003;4377-4392.
14. Baxter C.A.R., Richards H.C. J. Med. Chem. 15:1972;351.
15. Rao V.A., Jain P.C., Anand N. J. Med. Chem. 13:1970;516.
16. Ma D., Zhang Y., Yao J., Wu S., Tao F. J. Am. Chem. Soc. 120:1998;12459.
17. Clement J.-B., Hayes J.F., Sheldrake H.M., Sheldrake P.W., Wells A.S. Synlett. 2001;1423-1427.
18. Mancuso A.J., Swern D. Synthesis. 1981;165-185.