The synthesis of baclofen and GABOB via Rh(II) catalyzed intramolecular C-H insertion of α-diazoacetamides

Tetrahedron

Volumn 61, Issue 6, 2005, Pages 1579-1586

  Chen, Zhenliang ^a,b   Chen, Zhiyong ^a   Jiang, Yaozhong ^a   Hu, Wenhao ^a  

^a CHENGDU INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Lactam; Baclofen; C H Insertion; GABA; Gabapentin

Indexed keywords

4 AMINO 3 HYDROXYBUTYRIC ACID; ACETAMIDE DERIVATIVE; BACLOFEN; GABAPENTIN; GAMMA LACTAM DERIVATIVE; RHODIUM COMPLEX;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; DRUG SYNTHESIS; HYDROLYSIS KINETICS; PRIORITY JOURNAL;

INSERTION SEQUENCES;

EID: 12344288044     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.11.077     Document Type: Article

References (51)

1. P.W. Yuen, G.D. Kanter, C.P. Taylor, and M.G. Vertanian Bioorg. Med. Chem. Lett. 4 1994 823 826
2. R.B. Silverman, R. Andruszkiewicz, S.M. Nanavati, C.P. Taylor, and M.G. Vartanian J. Med. Chem. 34 1991 2295 2298
3. A.G. Moglioni, B.N. Brousse, A. Álvarez-Larena, G.Y. Moltrasio, and R.M. Ortuño Tetrahedron: Asymmetry 13 2002 451 454
4. J.S. Bryans, N. Davies, N.S. Gee, V.U.K. Dissanayake, and G.S. Ratcliffe J. Med. Chem. 41 1998 1838 1845
5. (a) Satzinger, G.; Hartenstein, J.; Herrmann, M.; Heldt, W. U.S. Pat. Appl. US 4,024,175, 1977.
6. (b) Geibel, W.; Hartenstein, J.; Herrmann, W.; Witzke, J. U.S. Pat. Appl. US 5,091,567, 1992.
7. (c) Stephen, B. J.; Morrell, A.; Ian, M. A. PCT WO 9,914,184, 1999.
8. (d) Steiner, K.; Herrmann, W.; Crone, G.; Combs, C.S. Appl. U.S. Pat. US 5,068,413, 1991.
9. M.J.S. Carpes, and C.R.D. Correia Tetrahedron Lett. 43 2002 741 744
10. C. Baldoli, S. Maiorana, E. Licandro, D. Perdicchia, and B. Vandoni Tetrehedron: Asymmetry 11 2000 2007 2014
11. C. Herdeis, and H.P. Hubmann Tetrehedron: Asymmetry 3 1992 1213 1221
12. M.X. Wang, and S.M. Zhao Tetrahedron Lett. 43 2002 6617 6620
13. C. Mazzini, J. Lebreton, V. Alphand, and R. Furstoss Tetrahedron Lett. 38 1997 1195 1196
14. E.J. Corey, and F.Y. Zhang Org. Lett. 2 2000 4257 4259
15. P. Resende, W.P. Almeida, and F. Coelho Tetrehedron: Asymmetry 10 1999 2113 2118
16. E. Brenna, N. Caraccia, C. Fuganti, D. Fuganti, and P. Grasselli Tetrehedron: Asymmetry 8 1997 3801 3805
17. R. Chênevert, and M. Desjjardins Tetrehedron Lett. 32 1991 4249 4250
18. N. Langlois, N. Dahuron, and H.S. Wang Tetrahedron 52 1996 15117 15126
19. M.P. Doyle, and W. Hu Chirality 14 2002 169 172
20. V.V. Thahur, M.D. Nikaljie, and A. Sudalai Tetrehedron: Asymmetry 14 2003 581 586
21. A.G.H. Wee, Q. Shi, Z. Wang, and K. Hatton Tetrehedron: Asymmetry 14 2003 897 909
22. E. Licandro, S. Maiorana, C. Baldoli, L. Capella, and D. Perdicchia Tetrehedron: Asymmetry 11 2000 975 980
23. B. Rajashekhar, and E.T. Kaiser J. Org. Chem. 50 1985 5480 5484
24. A.S. Gopalan, and C.J. Sih Tetrahedron Lett. 25 1984 5235 5238
25. J. Aubé, Y. Wang, S. Ghosh, and K.L. Langhans Synth. Commun. 21 1991 693 701
26. M. Larcheveque, and S. Henrot Tetrahedron 46 1990 4277 4282
27. B.E. Rossiter, and K.B. Sharpless J. Org. Chem. 49 1984 3707 3711
28. K. Ingelundt, and C. Pedersen Acta Chem. Scand. B 37 1983 341 344
29. P. Renaud, and D. Seebach Synthesis 1986 424 425
30. M.E. Jung, and T.J. Shaw J. Am. Chem. Soc. 102 1980 6304 6311
31. T. Ye, and M.A. Mckervey Chem. Rev. 94 1994 1091 1160
32. M.P. Doyle, M.A. Mckervey, and T. Ye Modern Catalytic Methods for Organic Synthesis With Diazo Compounds 1998 Wiley New York pp 129-139
33. M.P. Doyle, and D.C. Forbes Chem. Rev. 98 1998 911 936
34. C.A. Merlic, and A.L. Zechman Synthesis 2003 1137 1156
35. H.M.L. Davies, and R.E.J. Beckwith Chem. Rev. 103 2003 2861 2904
36. M. Anada, O. Mita, H. Watanabe, S. Kitagaki, and S. Hashimoto Synlett 1999 1775 1777
37. M.P. Doyle, and A.V. Kalinin Tetrahedron Lett. 37 1996 1371 1374
38. T.C. Smale Tetrahedron Lett. 25 1984 2913 2914
39. P. Brown, and R. Southgate Tetrahedron Lett. 27 1986 247 250
40. M. Anada, and S.I. Hashimoto Tetrahedron Lett. 39 1998 79 82
41. C.H. Yoon, A. Nagle, C. Chen, D. Gandhi, and K.W. Jung Org. Lett. 5 2003 2259 2262
42. A. Padwa, D.J. Austin, S.F. Hornbuckle, and M.A. Semones J. Am. Chem. Soc. 114 1992 1874 1876
43. A. Padwa, D.J. Austin, A.T. Price, M.A. Semones, M.P. Doyle, M.N. Protopopova, W.R. Winchester, and A. Tran J. Am. Chem. Soc. 115 1993 8669 8680
44. N. Watanabe, M. Anada, S. Hashimoto, and S. Ikegami Synlett 1994 1031 1033
45. C.H. Yoon, M.J. Zaworotko, B. Moulton, and K.W. Jung Org. Lett. 3 2001 3539 3542
46. C. Zhenliang, C. Zhiyong, J. Yaozhong, and H. Wenhao Synlett 2003 1965 1966
47. M.P. Doyle, M. Yan, I.M. Phillips, and D.J. Timmons Adv. Synth. Catal. 344 2002 91 95
48. A.G.H. Wee, B. Liu, and L. Zhang J. Org. Chem. 57 1992 4404 4414
49. M.P. Doyle, W. Hu, A.G.H. Wee, Z. Wang, and C. Duncan Org. Lett. 5 2003 407 410
50. M.J. Earle, R.A. Fairhurst, H. Heaney, and G. Papageorgiou Synlett 1990 621 623
51. S.H. Rosenberg, and H. Rapoport J. Org. Chem. 50 1985 3979 3982