Dirhodium catalyzed intramolecular enantioselective C-H insertion reaction of N-cumyl-N-(2-p-anisylethyl)diazoacetamide: Synthesis of (-)-Rolipram

Tetrahedron Asymmetry

Volumn 16, Issue 9, 2005, Pages 1693-1698

  Liu, Wei Jun ^a   Chen, Zhen Liang ^a   Chen, Zhi Yong ^a   Hu, Wen Hao ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

ACETAMIDE DERIVATIVE; AROMATIC COMPOUND; N CUMYL N (2 4 ANISYLETHYL)DIAZOACETAMIDE; RHODIUM DERIVATIVE; ROLIPRAM; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

EID: 17844404791     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.03.023     Document Type: Article

References (36)

1. M.P. Doyle, M.A. McKervey, and T. Ye Modern Catalytic Methods for Organic Synthesis with Diazo Compounds 1998 Wiley New York 129
2. M.P. Doyle, and D.C. Forbes Chem. Rev. 98 1998 911 935
3. C.A. Merlic, and A.L. Zechman Synthesis 2003 1137 1156
4. H.M.L. Davies, and R.E.J. Beckwith Chem. Rev. 103 2003 2861 2903
5. J.W. Bode, M.P. Doyle, M.N. Protopopova, and Q.-L. Zhou J. Org. Chem. 61 1996 9146 9155
6. M.P. Doyle, M.N. Protopopova, Q.-L. Zhou, J.W. Bode, S.H. Simonsen, and V. Lynch J. Org. Chem. 60 1995 6654 6655
7. M.P. Doyle, W. Hu, A.G.H. Wee, Z. Wang, and S.C. Duncan Org. Lett. 5 2003 407 410
8. A.G.H. Wee, and S.C. Duncan Tetrahedron Lett. 43 2002 6173 6176
9. M. Anada, and S. Hashimoto Tetrahedron Lett. 39 1998 79 82
10. C.H. Yoon, A. Nagle, C. Chen, D. Gandhi, and K.W. Jung Org. Lett. 5 2003 2259 2262
11. C.H. Yoon, M.J. Zaworotko, B. Moulton, and K.W. Jung Org. Lett. 3 2001 3539 3542
12. M.P. Doyle, M.N. Protopopova, W.R. Winchester, and K.L. Daniel Tetrahedron Lett. 33 1992 7819 7822
13. M.P. Doyle, M. Yan, I.M. Phillips, and D.J. Timmons Adv. Synth. Catal. 344 2002 91 95
14. A.G.H. Wee, B. Liu, and D.D. McLeod J. Org. Chem. 63 1998 4218 4227
15. F. Zargoza Tetrahedron 51 1995 8829 8834
16. Z. Chen, Z. Chen, Y. Jiang, and W. Hu Synlett 2004 1763 1764
17. H. Wachtel J. Pharm. Pharmacol. 35 1983 440
18. H.H. Schneider, R. Schmiechen, M. Brezinski, and J. Seidler Eur. J. Pharmacol. 127 1986 105
19. N.A. Saccomano, F.J. Vinick, B.K. Koe, J.A. Nielsen, W.M. Whalen, M. Meltz, D. Phillips, P.F. Thadieo, S. Jung, D.S. Chapin, L.A. Lebel, L.L. Russo, D.A. Helweg, J.L. Johnson, J.L. Ives Jr., and I.H. Williams J. Med. Chem. 34 1991 291 298
20. J.J. Bronson, I. Ghazzouli, M.J.M. Hitchcock, R.R. Webb II, and J.C. Martin J. Med. Chem. 32 1989 1457 1463
21. P.W. Baures, D.S. Eggleston, K.F. Erhard, L.B. Cielinski, T.J. Torphy, and S.B. Christensen J. Med. Chem. 36 1993 3274 3277
22. J. Barluenga, F. Aznar, and M.A. Palomero Chem. Eur. J. 7 2001 4323 5318
23. For a review, see: J. Mulzer J. Prakt. Chem. 336 1994 287 291
24. T. Honda, F. Ishikawa, K. Kanai, S. Sato, D. Kato, and H. Tominaga Heterocycles 42 1996 109 112
25. J. Alvarez-Builla, A. DÌaz, J.G. Siro, J.L. GarcÌa- NavÌo, and J.J. Vaquero Synthesis 1994 559 562
26. A.I. Meyers, and L. Snyder J. Org. Chem. 58 1993 36 42
27. J. Mulzer, R. Zuhse, and R. Schmiechen Angew. Chem. 104 1992 914 915
28. Angew. Chem., Int. Ed. Engl. 31 1992 870 872
29. K. Itoh, and S. Kanemasa J. Am. Chem. Soc. 124 2002 13394 13395
30. D.M. Barnes, J. Ji, M.G. Fickes, M.A. Fitzgerald, S.A. King, H.E. Morton, F.A. Plagge, M. Preskill, S.H. Wagaw, S.J. Wittenberger, and J. Zhang J. Am. Chem. Soc. 124 2002 13097 13105
31. J.M. Becht, O. Meyer, and G. Helmchen Synthesis 2003 2805 2810
32. M. Anada, O. Mita, H. Watanabe, S. Kitagaki, and S. Hashimoto Synlett 1999 1775 1777
33. 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
34. R.E. Zelle Synthesis 1991 1023 1028
35. Z. Du, Z. Chen, Z. Chen, X. Yu, and W. Hu Chirality 16 2004 516 519
36. 2/n-hexane (1/2)