Enantioselective syntheses of (R)-3-phenyl GABA, (R)-baclofen and 4-arylpyrrolidin-2-ones

Tetrahedron

Volumn 52, Issue 48, 1996, Pages 15117-15126

  Langlois, Nicole ^a   Dahuron, Nathalie ^a   Wang, Hai Shan ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDONE DERIVATIVE; 4 AMINO 3 PHENYLBUTYRIC ACID; BACLOFEN;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS; TECHNIQUE;

EID: 0030602254     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)00946-5     Document Type: Article

References (27)

1. 1. a) Bowery, N.G.; Hill, D.R.; Hudson, A.L.; Doble, A.; Middemiss, N.D.; Shaw, J.; Turnbull, M. Nature, 1980, 283, 92-94.
2. b) Silverman, R.B.; Levy, M.A. J. Biol. Chem., 1981, 256, 11565-11568.
3. 2. Allan, R.D.; Bates, M.C.; Drew, C.A.; Duke, R.K.; Hambley, T.W.; Johnston, G.A.R.; Mewett, K.N.; Spence, I. Tetrahedron, 1990, 46, 2511-2524.
4. 3. a) Bowery, N.E. Trends Pharm. Sci. 1982, 31, 400-403.
5. b) Olpe, H.R.; Demiéville, H.; Baltzer, V.; Bencze, W.L.; Koella, W.P.; Wolf, P.; Haas, H.L. Eur. J. Pharmacol., 1978, 52, 133-136.
6. 4. Schoenfelder, A.; Mann, A.; Le Coz, S. Synlett. 1992, 63-64.
7. 5. Herdeis, C.; Hubmann, H.P. Tetrahedron : Asymmetry 1992, 3, 1213-1221.
8. 6. Chênevert, R.; Desjardins, M. Can. J. Chem. 1994, 72, 2312-2317.
9. 7. Yoshifuji, S.; Kaname, M. Chem. Pharm. Bull. 1995, 43, 1302-1306.
10. 8. Dahuron, N.; Langlois, N. Synlett 1996, 51-52.
11. 9. Abiko, A.; Masamune, S. Tetrahedron Lett. 1992, 38, 5517-5518.
12. 10. Dahuron, N.; Langlois, N.; Chiaroni, A.; Riche, C. Heterocycles 1996, 42, 635-643.
13. 11. Dahuron, N. Ph.D. Thesis, Paris XI University, Orsay, 1995, Order n° 3998.
14. 12. Langlois, N.; Dahuron, N. Tetrahedron Lett. 1996, 37, 3993-3996.
15. 13. Satoh, T.; Suzuki, S.; Suzuki, Y.; Miyaji, Y.; Imai, Z. Tetrahedron Lett. 1969, 4555-4558.
16. 14. Ganem, B.; Osby, J.O. Chem. Rev. 1986, 86, 763-780.
17. 15. Itsuno, S.; Sakurai, Y.; Ito, K. Synthesis 1988, 995-996.
18. 16. Russell, T.W.; Hoy, R.C.; Cornelius, J.E. J. Org. Chem. 1972, 37, 3552-3553.
19. 17. Lu, Y.; Miet, C.; Kunesch, N.; Poisson, J.E. Tetrahedron : Asymmetry 1993, 4, 893-902.
20. 18. Nose, A.; Kudo, T. Chem. Pharm. Bull. 1981, 29, 1159-1161.
21. 19. Liu, Y.; Schwartz, J. Tetrahedron 1995, 51, 4471-4482.
22. 20. Mann, A.; Boulanger, T.; Brandau, B.; Durant, F.; Evrard, G.; Heaulme, M.; Desaulles, E.; Wermuth C.G. J. Med. Chem. 1991, 34, 1307-1313.
23. 21. "The Chemistry of Functional Groups" Editor. Patai, S., 1, Chap. 8, John Wiley and Sons, London 1975.
24. 22. Baggliolini, E.; Berscheis, H.G.; Bozzato, G.; Cavalieri, E.; Schaffner, K.; Jeger, O. Helv. Chim. Acta 1971, 54, 429-449.
25. 23. Zelle, R.E. Synthesis 1991, 1023-1026.
26. 24. a) Crider, A.M.; Andersen, P.H.; Cruse, S.F.; Ghosh, D.; Harpalani, A. Eur. J. Med. Chem. 1992, 27, 407-411.
27. b) Feldman, P.L.; Brackeen, M.F.; Cowan, D.J.; Marron, B.E.; Schoenen, F.J.; Stafford, J.A.; Suh, E.M.; Domanico, P.L.; Rose, D.; Leesnitzer, M.A.; Sloan Brawley, E.; Strickland, A.B.; Verghese, M.W.; Connolly K.M.; Bateman-Fite, R.; Staton Noel, L.; Sekut, L.; Stimpson, S.A. J. Med. Chem. 1995, 38, 1505-1510.