Asymmetric hydrogenation of 2-substituted N-protected-indoles catalyzed by rhodium complexes of BINOL-derived phosphoramidites

Tetrahedron Asymmetry

Volumn 21, Issue 1, 2010, Pages 7-10

  Mršić, Nataša ^a   Jerphagnon, Thomas ^a   Minnaard, Adriaan J ^a   Feringa, Ben L ^a   de Vries, Johannes G ^a,b  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b DSM Pharmaceutical Products   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

1 ACETYL 2,3 INDOLINE 2 CARBOXYLIC ACID; DIPEPTIDYL CARBOXYPEPTIDASE INHIBITOR; INDOLAPRIL; INDOLE DERIVATIVE; INDOLINE 2 CARBOXYLIC ACID; PENTOPRIL; PERINDOPRIL; PHOSPHORAMIDOUS ACID DERIVATIVE; RHODIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; HYDROGENATION; PRIORITY JOURNAL;

EID: 76049091228     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.11.017     Document Type: Article

References (47)

1. Bianchini C., Meli A., and Vizza F. In: de Vries J.G., and Elsevier C.J. (Eds). The Handbook of Homogeneous Hydrogenation Vol. 2 (2007), Wiley-VCH, Weinheim 455
2. Glorius F. Org. Biomol. Chem. 3 (2005) 4171
3. Zhou Y.-G. Acc. Chem. Res. 40 (2007) 1357
4. Remond, G.; Laubie, M.; Vincent, M. EP0049658, 1982, to Science Union et Cie Societé Française de Recherche Medical.
5. Ksander, G. M.; Zimmerman, M. B. EP0336950, 1992, to Ciba-Geigy AG.
6. Buzby, G. C. US4520205, 1985, to American Home Products.
7. Miyata, S.; Fukuda, H.; Imamura, S. EP0171616, 1986, to Toray Industries.
8. Wang, Z.-X.; Raheem, M. A.; Weeratunga, G. WO2006053440, 2006, to Apotex Pharmachem, Inc.
9. Vincent M., Rémond G., Portevin B., Serkiz B., and Laubie M. Tetrahedron Lett. 23 (1982) 1677
10. Hendrickx, A. J. J.; Kuilman, T. EP0937714, 1999, to DSM NV.
11. Chava, S.; Bandari, M.; Madhuresh, K. S. WO2006013581, 2006, to Matrix Lab Ltd.
12. Fujino, T.; Ogawa, R.; Sato, H. JP2004182670, 2004, to Toray Industries.
13. Souvie, J.-C.; Lecouve, J.-P., 2003, to Les Laboratoires Servier.
14. Vlattas, I. US4665087, 1987, to Ciba-Geigy Corporation.
15. Buzby, G. C.; Winkley, M. W.; Mccaully, R. J. US4614806 1986, to American Home Products.
16. Asada, M.; Hamaguchi, S.; Kutsuki, H.; Nakamura, Y.; Takashi, H.; Takahara, K.; Shimada, Y.; Ohashi, T.; Watanabe, K. US4898822, 1990, to Kanegafuchi Chemical Industry.
17. Le Goffic, F. FR2883874, 2006, to Laboratoire Substipharm.
18. Cho, N. R.; Lim, J. H.; Kim, J. K. WO2005051910, 2005, to SK Corporation.
19. Ghisalba, O.; Ramos, G.; Schaer, H. P. DE 3727411 A1, 1988, to Ciba-Geigy AG.
20. de Vries, A. H. M.; de Vries, J. G.; van Assema, F. B. J.; de Lange, B.; Mink, D.; Hyett, D. J.; Maas, P. J. D. WO2006069799, 2006, to DSM IP Assets bv.
21. Arp F.O., and Fu G.C. J. Am. Chem. Soc. 128 (2006) 14264
22. Kuwano R., Sato K., Kurokawa T., Karube D., and Ito Y. J. Am. Chem. Soc. 122 (2000) 7614
23. Kuwano R., Kaneda K., Ito T., Sato K., Kurokawa T., and Ito Y. Org. Lett. 6 (2004) 2213
24. Kuwano R., and Kashiwabara M. Org. Lett. 8 (2006) 2653
25. Kuwano R., Kashiwabara M., Sato K., Ito T., Kaneda K., and Ito Y. Tetrahedron: Asymmetry 17 (2006) 521
26. van den Berg M., Minnaard A.J., Schudde E.P., van Esch J., de Vries A.H.M., de Vries J.G., and Feringa B.L. J. Am. Chem. Soc. 122 (2000) 11539
27. van den Berg, M.; Minnaard, A. J.; de Vries, J. G.; Feringa, B. L. WO0204466, 2002, to DSM N.V.
28. Jerphagnon T., Renaud J.-L., and Bruneau C. Tetrahedron: Asymmetry 15 (2004) 2101
29. Minnaard A.J., Feringa B.L., Lefort L., and de Vries J.G. Acc. Chem. Res. 40 (2007) 1267
30. de Vries, J. G.; Stegink, B. WO2008/077610, 2008, to DSM IP Assets N.V.
31. Mršić N., Lefort L., Boogers J.A.F., Minnaard A.J., Feringa B.L., and de Vries J.G. Adv. Synth. Catal. 350 (2008) 1081
32. Lefort L., Boogers J.A.F., de Vries A.H.M., Ager D.J., Jagt R.B.C., Minnaard A.J., Feringa B.L., and de Vries J.G. Chim. Oggi 26 (2008) 26
33. Lefort L., Boogers J.A.F., de Vries A.H.M., and de Vries J.G. Org. Lett. 6 (2004) 1733
34. Jagt R.B.C., Toullec P.Y., Schudde E.P., de Vries J.G., Feringa B.L., and Minnaard A.J. J. Comb. Chem. 9 (2007) 407
35. de Vries J.G., and Lefort L. Chem. Eur. J. 12 (2006) 4722
36. Hoen R., Boogers J.A.F., Bernsmann H., Minnaard A.J., Meetsma A., Tiemersma-Wegman T.D., de Vries A.H.M., de Vries J.G., and Feringa B.L. Angew. Chem., Int. Ed. 44 (2005) 4209
37. Hoen R., Tiemersma-Wegman T.D., Procuranti B., Lefort L., De Vries J.G., Minnaard A.J., and Feringa B.L. Org. Biomol. Chem. 5 (2007) 267
38. Peña D., Minnaard A.J., Boogers J.A.F., de Vries A.H.M., de Vries J.G., and Feringa B.L. Org. Biomol. Chem. 1 (2003) 1087
39. Mršić N., Lefort L., Boogers J.A.F., Minnaard A.J., Feringa B.L., and de Vries J.G. Adv. Synth. Catal. 350 (2008) 1081
40. Reetz M.T., Sell T., Meiswinkel A., and Mehler G. Angew. Chem., Int. Ed. 42 (2003) 790
41. Reetz M.T., and Mehler G. Tetrahedron Lett. 44 (2003) 4593
42. Reetz M.T. Angew. Chem., Int. Ed. 47 (2008) 2556
43. Morris R.H. In: de Vries J.G., and Elsevier C.J. (Eds). Handbook of Homogeneous Hydrogenation (2007), Wiley-VCH, Weinheim
44. Trzeciak A.M., Głowiak T., and Ziółkowski J.J. J. Organomet. Chem. 552 (1998) 159
45. Arnold L.A., Imbos R., Mandoli A., de Vries A.H.M., Naasz R., and Feringa B.L. Tetrahedron 56 (2000) 2865
46. Bernsmann H., van den Berg M., Hoen R., Minnaard A.J., Mehler G., Reetz M.T., de Vries J.G., and Feringa B.L. J. Org. Chem. 70 (2005) 943
47. Maciá B., Fernández-Ibáñez M.A., Mršić N., Minnaard A.J., and Feringa B.L. Tetrahedron Lett. 49 (2008) 1877