Asymmetric rhodium-catalyzed hydrogenation meets gold-catalyzed cyclization: Enantioselective synthesis of 8-hydroxytetrahydroisoquinolines

Chemistry - A European Journal

Volumn 12, Issue 20, 2006, Pages 5376-5382

  Hashmi, A Stephen K ^a   Haufe, Patrick ^a   Schmid, Christoph ^a   Nass, Andreas Rivas ^b   Frey, Wolfgang ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

^b UMICORE AG AND CO KG   (Germany)

Author keywords

Catalysis; Cyclization; Gold; Homogeneous; Rhodium; Symmetric hydrog nation

Indexed keywords

CYCLIZATION; HOMOGENEOUS; SYMMETRIC HYDROGÉNATION;

AMINO ACIDS; CATALYSIS; CATALYST SELECTIVITY; GOLD; NITROGEN COMPOUNDS; RHODIUM; SYNTHESIS (CHEMICAL);

HYDROGENATION;

GOLD; LIGAND; RHODIUM; TETRAHYDROISOQUINOLINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; HYDROGENATION; MASS SPECTROMETRY; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CATALYSIS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; GOLD; HYDROGENATION; LIGANDS; MASS SPECTROMETRY; RHODIUM; STEREOISOMERISM; TETRAHYDROISOQUINOLINES;

EID: 33745928459     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200600192     Document Type: Article

References (48)

1. J. D. Scott, R. M. Williams, Chem. Rev. 2002, 102, 1669-1730.
2. http://www.pharmamar.com/en/press/.
3. A. Bischler, B. Napieralski, Ber. Dtsch. Chem. Ges. A 1893, 26, 1903-1908.
4. a) C. Pomeranz, Monatsh. Chem. 1893, 14, 116-119;
5. b) P. Fritsch, Ber. Dtsch. Chem. Ges. A 1893, 26, 419-422.
6. A. Pictet, T. Spengler, Ber. Dtsch. Chem. Ges. A 1911, 44, 2030-2036.
7. O. Koepler, S. Laschat, A. Baro, P. Fischer, B. Miehlich, M. Hotfilder, C. le Viseur, Eur. J. Org. Chem. 2004, 3611-3622.
8. a) A. S. K. Hashmi, T. M. Frost, J. W. Bats, J. Am. Chem. Soc. 2000, 122, 11553-11554;
9. b) A. S. K. Hashmi, T. M. Frost, J. W. Bats, Org. Lett. 2001, 3, 3769-3771;
10. c) A. S. K. Hashmi, T. M. Frost, J. W. Bats, Catal. Today 2002, 72, 19-72.
11. A. S. K. Hashmi, L. Ding, J. W. Bats, P. Fischer, W. Frey, Chem. Eur. J. 2003, 9, 4339-4345.
12. a) A. S. K. Hashmi, J. P. Weyrauch, M. Rudolph, E. Kurpejovic, Angew. Chem. 2004, 116, 6707-6709;
13. Angew. Chem. Int. Ed. 2004, 43, 6545-6547;
14. b) A. S. K. Hashmi, M. Rudolph, J. P. Weyrauch, M. Wölfle, W. Frey, J. W. Bats, Angew. Chem. 2005, 117, 2858-2861;
15. Angew. Chem. Int. Ed. 2005, 44, 2798-2801.
16. C. Cativiela, J. A. Mayoral, E. Meléndez, L. A. Oro, M. T. Pinillos, R. Usón, J. Org. Chem. 1984, 49, 2502-2504.
17. H. W. Krause, F.W. Wilcke, H.-J. Kreuzfeld, C. Döbler, Chirality 1992, 4, 110-115.
18. T. Masquelin, E. Broger, K. Müller, R. Schmid, D. Obrecht, Helv. Chim. Acta 1994, 77, 1395-1411.
19. a) M. J. Burk, J. R. Lee, J. P. Martinez, J. Am. Chem. Soc. 1994, 116, 10847-10848;
20. b) A. S. C. Chan, W. Hu, C.-C. Pai, C.-P- Lau, Y. Jiang, A. Mi, M. Yan, J. Sun, R. Lou, J. Deng, J. Am. Chem. Soc. 1997, 119, 9570-9571;
21. c) X. Li, R. Lou, C.-H. Yeung, A. S. C. Chan, W. K. Wong, Tetrahedron: Asymmetry 2000, 11, 2077-2082;
22. d) F.-Y. Zhang, W. K. Wong, A. S. C. Chan, Tetrahedron: Asymmetry 2001, 12, 2337-2342;
23. e) R. Guo, X. Li, J. Wu, W.H. Kwok, J. Chen, M. C. K. Choi, A. S. C. Chan, Tetrahedron Lett. 2002, 43, 6803-6806;
24. f) Q. Zeng, H. Liu, A. Mi, Y. Jiang, X. Li, M. C. K. Choi, A. S. C. Chan, Tetrahedron 2002, 58, 8799-8803;
25. g) R. Guo, T. T.-L. Au-Yeung, J. Wu, M. C. K. Choi, A. S. C. Chan, Tetrahedron: Asymmetry 2002, 13, 2519-2522;
26. h) C. W. Lin, C.-C. Lin, L. F.-L. Lam, T. T.-L. Au-Yeung, A. S. C. Chan, Tetrahedron Lett. 2004, 45, 7379-7381;
27. N. W. Boaz, E. B. Mackenzie, S. D. Debenham, S. E. Large, J. A. Ponasik, Jr., J. Org. Chem. 2005, 70, 1872-1880.
28. U. Schmidt, A. Lieberknecht, J. Wild, Synthesis 1984, 53-60.
29. CCDC 294763 (rac-15f), CCDC 294765 ((-)-15f) and CCDC 294764 ((R)-23a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
30. T. Miyazawa, Y. Shindo, T. Yamada, S. Kuwata, Anal. Lett. 1993, 26, 457-473.
31. R. Uson, A. Laguna, M. V. Castrillo, Synth. React. Inorg. Met.-Org. Chem. 1979, 9, 317-324;
32. for the first application as a catalyst see: A. S. K. Hashmi, M. C. Blanco, E. Kurpejović, W. Frey, J. W. Bats, Adv. Synth. Catal. 2006, 348, 709-713.
33. a) Y. Fukuda, K. Utimoto, H. Nozaki, Heterocycles 1987, 25, 297-300; b)
34. Y. Fukuda, K. Utimoto, Synthesis 1991, 975-978;
35. c) Y. Fukuda, K. Utimoto, Bull. Chem. Soc. Jpn. 1991, 64, 2013-2015;
36. d) J. H. Teles, M. Schulz (BASF AG), WO-A1 9721648, 1997.
37. [Chem. Abstr. 1997, 127, 121499];
38. e) J. H. Teles, S. Brode, M. Chabanas, Angew. Chem. 1998, 110, 1475-1478;
39. Angew. Chem. Int. Ed. 1998, 37, 1415-1418;
40. f) A. Arcadi, S. Di Giuseppe, F Marinelli, E. Rossi, Adv. Synth. Catal. 2001, 343, 443-446;
41. g) E. Mizushima, K. Sato, T. Hayashi, M. Tanaka, Angew. Chem. 2002, 114, 4745-4747;
42. Angew. Chem. Int. Ed. 2002, 41, 4563-4565;
43. h) E. Mizushima, T. Hayashi, M. Tanaka, Org. Lett. 2003, 5, 3349-3352;
44. P. Roembke, H. Schmidbaur, S. Cronje, H. Raubenheimer, J. Mol. Catal. A 2004, 2/2, 35-42;
45. j) S. Antoniotti, E. Genin, V. Michelet, J.-P. Genet, J. Am. Chem. Soc. 2005, 127, 9976-9977;
46. k) L. Zhang, S. A. Kozmin, J. Am. Chem. Soc. 2005, 127, 6962-6963.
47. A. Bayler, A. Bauer, H. Schmidbaur, Chem. Ber. 1997, 130, 115-118.
48. B. Martín-Matute, C. Nevado, D. J. Cárdenas, A. M. Echavarren, J. Am. Chem. Soc. 2003, 125, 5757-5766.