Efficient enantioselective synthesis of 3-aminochroman derivatives through ruthenium-synphos catalyzed asymmetric hydrogenation

Organic Letters

Volumn 13, Issue 15, 2011, Pages 3782-3785

  Wu, Zi ^a,b   Ayad, Tahar ^a,b   Ratovelomanana Vidal, Virginie ^a,b  

^a PSL RESEARCH UNIVERSITY   (France)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

3 AMINOCHROMAN; 3-AMINOCHROMAN; CHROMAN DERIVATIVE; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGENATION; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; CHROMANS; HYDROGENATION; MOLECULAR STRUCTURE; RUTHENIUM; STEREOISOMERISM;

EID: 79961068521     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol201786q     Document Type: Article

References (49)

1. Anderson, B. R.; Carlsson, P. A. E.; Svensson, K. A. I.; Wikstron, H. V.; Hallberg, A. R. WO90/12795, 1990.
2. Cook, A.; Miller, D. C. WO2006/056850, 2006.
3. Hatzenbuhler, N. T.; Baudy, R.; Evrard, D. A.; Failli, A.; Harrison, B. L.; Lenicek, S.; Mewshaw, R. E.; Saab, A.; Shah, U.; Sze, J.; Zhang, M.; Zhou, D.; Chlenov, M.; Kagan, M.; Golembieski, J.; Hornby, G.; Lai, M.; Smith, D. L.; Sullivan, K. M.; Schechter, L. E.; Andree, T. H. J. Med. Chem. 2008, 51, 6980
4. Ross, S. B.; Thorberg, S.-O.; Jerning, E.; Mohell, N.; Stenfors, C.; Wallsten, C.; Milchert, I. G.; Ojteg, G. A. CNS Drug Rev. 1999, 5, 213
5. Curle, P. F.; Mocaer, E.; Renard, P.; Guardiola, B. Drug Dev. Res. 1994, 32, 183
6. MacSweeney, C. P.; Lésourd, M.; Gandon, J.-M. Eur. J. Pharmacol. 1998, 345, 133
7. Learmonth, D. A.; Soares Da Silva, P. M. V.; Beliaev, A. WO2004/033447, 2004.
8. Holmberg, P.; Tedenborg, L.; Rosqvist, S.; Johansson, A. M. Bioorg. Med. Chem. Lett. 2005, 15, 747
9. Holmberg, P.; Sohn, D.; Leideborg, R.; Caldirola, P.; Zlatoidsky, P.; Sverker, H.; Mohell, N.; Rosqvist, S.; Nordvall, G.; Johansson, A. M.; Johansson, R. J. Med. Chem. 2004, 47, 3927
10. Zhou, D.; Hatzenbuhler, N. T.; Gross, J. L.; Harrison, B. L.; Evrard, D. A.; Chlenov, M.; Golembiesky, J.; Hornby, G.; Schechter, L. E.; Smith, D. L.; Andree, T. H.; Stack, G. P. Bioorg. Med. Chem. Lett. 2007, 17, 3117
11. Usse, S.; Pave, G.; Guillaumet, G.; Viaud-Massuard, M.-C. Tetrahedron: Asymmetry 2001, 12, 1689
12. Pave, G.; Usse-Versluys, S.; Viaud-Massuard, M.-C.; Guillaumet, G. Org. Lett. 2003, 23, 4253
13. Fuganti, C.; Sacchetti, A. J. Mol. Catal. B: Enzym. 2010, 66, 276
14. Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis, 2 nd ed.; Ojima, I., Ed.; John Wiley & Sons: New York, 2000; pp 1-110.
15. Noyori, R. Angew. Chem., Int. Ed. 2002, 41, 2008
16. Shang, G.; Li, W.; Zhang, X. In Catalytic Asymmetric Synthesis, 3 rd ed.; Ojima, I., Ed.; John Wiley & Sons: New York, 2010; pp 343-436.
17. Genet, J.-P. Acc. Chem. Res. 2003, 36, 908
18. de Vries, A.-G.; Elsevier, C. J., Eds. Handbook of Homogeneous Hydrogenation; Wiley-VCH: Weinheim, Germany, 2006.
19. Zhang, Z.; Zhu, G.; Jiang, Q.; Xiao, D.; Zhang, X. J. Org. Chem. 1999, 64, 1774
20. Tang, W.; Chi, Y.; Zhang, X. Org. Lett. 2002, 4, 1696
21. Bernsmann, H.; Van Der Berg, M.; Hoen, R.; Minnard, A. J.; Mehler, G.; Reetz, M. T.; De Vries, J. G.; Feringa, B. L. J. Org. Chem. 2005, 70, 943
22. Dupau, P.; Bruneau, C.; Dixneuf, P. H. Tetrahedron: Asymmetry 1999, 10, 3467
23. Dupau, P.; Le Gendre, P.; Bruneau, C.; Dixneuf, P. H. Synlett 1999, 11, 1832
24. Renaud, J. L.; Dupau, P.; Hay, A.-E.; Guingouain, M.; Dixneuf, P. H.; Bruneau, C. Adv. Synth. Catal. 2003, 345, 230
25. Learmonth, D. A.; Gerosa, A. Z.; Grasa, G. A.; Beliaev, A. US2010/0036127, 2010.
26. Mordant, C.; Reymond, S.; Tone, H.; Lavergne, D.; Touati, R.; Ben Hassine, B.; Ratovelomanana-Vidal, V.; Genet, J.-P. Tetrahedron 2007, 63, 6115
27. Blanc, D.; Madec, J.; Popowyck, F.; Ayad, T.; Phansavath, P.; Ratovelomanana-Vidal, V.; Genet, J.-P. Adv. Synth. Catal. 2007, 349, 942
28. Jeulin, S.; Ayad, T.; Ratovelomanana-Vidal, V.; Genet, J.-P. Adv. Synth. Catal. 2007, 349, 1592
29. Deport, C.; Buchotte, M.; Abecassis, K.; Tadaoka, H.; Ayad, T.; Ohshima, T.; Genet, J.-P.; Mashima, K.; Ratovelomanana-Vidal, V. Synlett 2007, 2743
30. Pautigny, C.; Jeulin, S.; Ayad, T.; Genet, J.-P.; Ratovelomanana-Vidal, V. Adv. Synth. Catal. 2008, 350, 2525
31. Tone, H.; Buchotte, M.; Mordant, C.; Guittet, E.; Ayad, T.; Ratovelomanana-Vidal, V. Org. Lett. 2009, 11, 1995
32. Tadaoka, H.; Cartigny, D.; Nagano, T.; Gosavi, T.; Ayad, T.; Genet, J.-P.; Ohshima, T.; Ratovelomanana-Vidal, V.; Mashima, K. Chem.-Eur. J. 2009, 15, 9990
33. Cartigny, D.; Nagano, T.; Ayad, T.; Genet, J.-P.; Ohshima, T.; Mashima, K.; Ratovelomanana-Vidal, V. Adv. Synth. Catal. 2010, 358, 1886
34. Prevost, S.; Gauthier, S.; Caňo de Andrade, M. C.; Mordant, C.; Touati, A. R.; Lesot, P.; Savignac, P.; Ayad, T.; Phansavath, P.; Ratovelomanana-Vidal, V.; Genet, J.-P. Tetrahedron: Asymmetry 2010, 21, 1436
35. Pautigny, C.; Debouit, C.; Vayron, P.; Ayad, T.; Ratovelomanana-Vidal, V. Tetrahedron: Asymmetry 2010, 21, 1382
36. Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi., K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932
37. Schmid, R.; Broger, E. A.; Cereghetti, M.; Crameri, Y.; Foricher, J.; Lalonde, M.; Müller, R. K.; Scalone, M.; Schoettel, G.; Zutter, U. Pure Appl. Chem. 1996, 68, 131
38. Duprat de Paule, S.; Champion, N.; Ratovelomanana-Vidal, V.; Genet, J.-P.; Dellis, P. French Patent 2830254, 2001.
39. Duprat de Paule, S.; Champion, N.; Ratovelomanana-Vidal, V.; Genet, J.-P.; Dellis, P. WO Patent 03029259, 2003.
40. Duprat de Paule, S.; Jeulin, S.; Ratovelomanana-Vidal, V.; Genet, J.-P.; Champion, N.; Dellis, P. Eur. J. Org. Chem. 2003, 1931
41. Duprat de Paule, S.; Jeulin, S.; Ratovelomanana-Vidal, V.; Genet, J.-P.; Champion, N.; Deschaux, G.; Dellis, P. Org. Process Res. Dev. 2003, 7, 399
42. Jeulin, S.; Duprat de Paule, S.; V. Ratovelomanana-Vidal, V.; Genet, J.-P.; Champion, N. Angew. Chem., Int. Ed. 2004, 43, 320
43. Jeulin, S.; Duprat de Paule, S.; V. Ratovelomanana-Vidal, V.; Genet, J.-P.; Champion, N.; Dellis, P. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5799
44. Genet, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Caño de Andrade, M. C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 665
45. Dobbs, D. A.; Vanhessche, K. P. M.; Brazi, E.; Rautenstrauch, V.; Lenoir, J. Y.; Genet, J. P.; Wiles, J. A.; Bergens, S. H. Angew. Chem., Int. Ed. 2000, 39, 1992
46. Wiles, J. A.; Bergens, S. H.; Vanhessche, K. P. M.; Dobbs, D. A.; Rautenstrauch, V. Angew. Chem., Int. Ed. 2001, 40, 914
47. Velkov, J.; Mincheva, Z.; Bary, J.; Boireau, G.; Fujier, C. Synth. Commun. 1997, 27, 375
48. Alami, M.; Peyrat, J.-F.; Belachmi, L.; Brion, J.-D. Eur. J. Org. Chem. 2001, 4207
49. Pavé, G.; Chalard, P.; Viaud-Massuard, M. C.; Troin, Y.; Guillaumet, G. Synthesis 2004, 121