Asymmetric synthesis of 3-hetero-substituted 2,3-dihydro-1H-isoindol-1-ones

Tetrahedron Asymmetry

Volumn 16, Issue 4, 2005, Pages 875-881

  Deniau, Eric ^a   Enders, Dieter ^b   Couture, Axel ^a   Grandclaudon, Pierre ^a  

^a UNITÉ DE CATALYSE ET DE CHIMIE DU SOLIDE   (France)

^b RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 (2 BENZYLOXYMETHYLPYRROLIDIN 1 YL) 3 BISPHENYLPHOSPHINOYL 2,3 DIHYDRO 1H ISOINDOL 1 ONE; 2 (2 METHOXYMETHYLPYRROLIDIN 1 YL) 3 (TOLUENE 4 SULFONYL) 2,3 DIHYDRO 1H ISOINDOL 1 ONE; 2 (2 METHOXYMETHYLPYRROLIDIN 1 YL) 3 [BIS(4 METHOXYPHENYL)PHOSPHINOYL] 2,3 DIHYDRO 1H ISOINDOL 1 ONE; 2 (2 METHOXYMETHYLPYRROLIDIN 1 YL) 3 [BIS(NAPHTH 2 YL)PHOSPHINOYL] 2,3 DIHYDRO 1H ISOINDOL 1 ONE; 3 (1H BENZOTRIAZOL 1 YL) 2 (2 BENZYLOXYMETHYLPYRROLIDIN 1 YL) 2,3 DIHYDRO 1H ISOINDOL 1 ONE; 3 (1H BENZOTRIAZOL 1 YL) 2 (2 METHOXYMETHYLPYRROLIDIN 1 YL) 2,3 DIHYDRO 1H ISOINDOL 1 ONE; 3 (1H BENZOTRIAZOL 1 YL) 2,3 DIHYDRO 1H ISOINDOL 1 ONE; 3 (4 CHLOROBENZENESULFONYL) 2 (2 METHOXYMETHYLPYRROLIDIN 1 YL) 2,3 DIHYDRO 1H ISOINDOL 1 ONE; 3 (4 CHLOROBENZENESULFONYL) 2,3 DIHYDRO 1H ISOINDOL 1 ONE; 3 (TOLUENE 4 SULFONYL) 2,3 DIHYDRO 1H ISOINDOL 1 ONE; 3 BENZENESULFONYL 2 (2 METHOXYMETHYLPYRROLIDIN 1 YL) 2,3 DIHYDRO 1H ISOINDOL 1 ONE; 3 BENZENESULFONYL 2,3 DIHYDRO 1H ISOINDOL 1 ONE; 3 DIPHENYLPHOSPHINOYL 2 (2 METHOXYMETHYLPYRROLIDIN 1 YL) 2,3 DIHYDRO 1H ISOINDOL 1 ONE; 3 DIPHENYLPHOSPHINOYL 2,3 DIHYDRO 1H ISOINDOL 1 ONE; 3 [BIS(4 METHOXYPHENYL)PHOSPHINOYL] 2,3 DIHYDRO 1H ISOINDOL 1 ONE; 3 [BIS(NAPTH 2 YL)PHOSPHINOYL] 2,3 DIHYDRO 1H ISOINDOL 1 ONE; HYDRAZONE DERIVATIVE; ISOINDOLE DERIVATIVE; NITROGEN; PEROXYPHTHALATE MAGNESIUM; PHTHALIC ACID DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ACIDITY; ADDITION REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL BOND; CHIRALITY; DEGRADATION; DEGRADATION KINETICS; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; OXIDATION KINETICS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; X RAY CRYSTALLOGRAPHY;

EID: 13844294123     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.01.012     Document Type: Article

References (40)

1. E. Valencia, I. Weiss, S. Firdous, A.J. Freyer, M. Shamma, A. Urzua, and V. Fayardo Tetrahedron 40 1984 3957 3962
2. F.G. Fang, and S.J. Danishefsky Tetrahedron Lett. 30 1989 2747 2750
3. A. Couture, E. Deniau, P. Grandclaudon, and C. Hoarau Tetrahedron 56 2000 1491 1499
4. V. Rys, A. Couture, E. Deniau, and P. Grandclaudon Eur. J. Org. Chem. 2003 1231 1237
5. A. Moreau, A. Couture, E. Deniau, and P. Grandclaudon Tetrahedron 60 2004 6169 6176
6. A. Moreau, A. Couture, E. Deniau, and P. Grandclaudon J. Org. Chem. 69 2004 4527 4530
7. A. Mertens, H. Zilch, B. Koenig, W. Schaefer, T. Poll, W. Kampe, H. Seidel, U. Leser, and H. Leinert J. Med. Chem. 36 1993 2526 2535
8. G. Maass, U. Immendoerfer, B. Koenig, U. Leser, B. Mueller, R. Goody, and E. Pfaff Antimicrob. Agents Chemother. 37 1993 2612 2617
9. R. Jingshan, R.M. Esnouf, A.L. Hopkins, D.I. Stuart, and D.K. Stammers J. Med. Chem. 42 1999 3845 3851
10. M. Ogata, H. Matsumoto, and K. Tawara Eur. J. Med. Chem. Chim. Ther. 16 1981 373 378
11. J.A. Hadfield, V.H. Pavlidis, and J.R.A. Roffey Synth. Commun. 25 1995 1319 1330
12. U. Holzgrabe, W. Bender, H.M. Botero Cid, M. Staudt, R. Pick, C. Pfletschinger, E. Balatkova, C. Traenkle, and K. Mohr Pharm. Acta Helv. 74 2000 149 155
13. H.M. Botero Cid, C. Traenkle, K. Baumann, R. Pick, E. Mies-Klomfass, E. Kostenis, K. Mohr, and U. Holzgrabe J. Med. Chem. 43 2000 2155 2164
14. F.A. Luzzio, and D.P. Zacherl Tetrahedron Lett. 39 1998 2285 2288
15. C. Hoarau, A. Couture, E. Deniau, and P. Grandclaudon Synthesis 2000 655 660
16. E. Deniau, and D. Enders Tetrahedron 57 2001 2581 2588
17. R. Hunter, and P. Richards Org. Biomol. Chem. 1 2003 2348 2356
18. A. Couture, E. Deniau, and P. Grandclaudon Tetrahedron 53 1997 10313 10330
19. E. Deniau, and D. Enders Tetrahedron Lett. 43 2002 8055 8058
20. Y. Ukaji, K. Tsukamoto, Y. Nasada, M. Shimizu, and T. Fujisawa Chem. Lett. 1993 221 224
21. S.M. Allin, C.J. Northfield, M.I. Page, and A.M.Z. Slawin J. Chem. Soc., Perkin Trans. 1 2000 1715 1721
22. R. Alonso, L. Castedo, and D. Dominguez Tetrahedron 26 1985 2925 2928
23. A.A. Bahajaj, and J.M. Vernon J. Chem. Soc., Perkin Trans. 1 1996 1041 1046
24. A.R. Katritzky, R. Maimait, Y.-J. Xu, and R.G. Akhmedova Synthesis 2002 601 604
25. T.R. Belliotti, W.A. Brink, S.R. Kesten, J.R. Rubin, D.J. Wustrow, K.T. Zoski, S.Z. Whetzel, A.E. Corbin, T.A. Pugsley, T.G. Heffner, and L.D. Wise Bioorg. Med. Chem. Lett. 8 1998 1499 1502
26. J.L. Wood, D.T. Petsch, B.M. Stoltz, E.M. Hawkins, D. Elbaum, and D.R. Stover Synthesis 1999 1529 1533
27. A.C. Bishop, J.A. Ubersax, D.T. Petsch, D.P. Matheos, N.S. Gray, J. Blethrow, E. Shimizu, J.Z. Tsien, P.G. Schultz, M.D. Rose, J.L. Wood, D.O. Morgan, and K.M. Shokat Nature (London) 407 2000 395 401
28. S.M. Allin, D.G. Vaidya, M.I. Page, A.M.Z. Slawin, and T. Smith Tetrahedron Lett. 41 2000 2219 2222
29. A.R. Katritzky, H.-Y. He, and A.K. Verma Tetrahedron: Asymmetry 13 2002 933 938
30. Review: D. Enders, and M. Klatt Synthesis 1996 1403 1418
31. E. Deniau, D. Enders, A. Couture, and P. Grandclaudon Tetrahedron: Asymmetry 14 2003 2253 2258
32. Review: A. Job, C.F. Janeck, W. Bettray, R. Peters, and D. Enders Tetrahedron 58 2002 2253 2329
33. H. Suzuki, S. Aoyagi, and C. Kibayashi Tetrahedron Lett. 35 1994 6119 6122
34. H. Suzuki, S. Aoyagi, and C. Kibayashi J. Org. Chem. 60 1995 6114 6122
35. R. Fernandez, A. Ferrete, J.M. Lassaletta, J.M. Llera, and A. Monge Angew. Chem., Int. Ed. 39 2000 2893 2897
36. D. Enders, V. Braig, and G. Raabe Can. J. Chem. 79 2001 1528 1535
37. R. Fernandez, A. Ferrete, J.M. Lassaletta, J.M. Llera, and E. Martin-Zamora Angew. Chem., Int. Ed. 41 2002 831 833
38. M.M. Kabat, L.M. Garofalo, A.R. Daniewski, S.D. Hutchings, W. Liu, M. Okabe, R. Radinov, and Y. Zhou J. Org. Chem. 66 2001 6141 6150
39. C.F. Hobbs, and W.S. Knowless J. Org. Chem. 46 1981 4422 4427
40. G.M. Sheldrick shelxtl, Program for Crystal Structure Solution and Refinement 1997 Bruker AXS Inc. Madison, WI