Catalytic enantioselective intramolecular redox reactions: Ring-fused tetrahydroquinolines

Journal of the American Chemical Society

Volumn 131, Issue 37, 2009, Pages 13226-13227

  Murarka, Sandip ^a   Deb, Indubhusan ^a   Zhang, Chen ^a   Seidel, Daniel ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; ENANTIOSELECTIVE; HIGH ENANTIOSELECTIVITY; REACTION CASCADES;

ENANTIOSELECTIVITY;

REDOX REACTIONS;

QUINOLINE DERIVATIVE;

ARTICLE; BIOTRANSFORMATION; CATALYSIS; CHELATION; CHEMICAL BOND; DIASTEREOISOMER; ENANTIOMER; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OXIDATION REDUCTION REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 70349399209     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja905213f     Document Type: Article

References (53)

1. For reviews on C-H bond functionalizations, see:(a) Godula, K.; Sames, D. Science 2006, 312, 67.
2. (b) Dick, A. R.; Sanford, M. S. Tetrahedron 2006, 62, 2439.
3. (c) Davies, H. M. L. Angew. Chem., Int. Ed. 2006, 45, 6422.
4. (d) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
5. (e) Bergman, R. G. Nature 2007, 446, 391.
6. (f) Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417.
7. (g) Thansandote, P.; Lautens, M. Chem.-Eur. J. 2009, 15, 5874.
8. (h) Li, C.-J. Acc. Chem. Res. 2009, 42, 335.
9. 3 C-H bonds adjacent to nitrogen in heterocycles, see:Campos, K. R. Chem. Soc. Rev. 2007, 36, 1069.
10. (a) Pastine, S. J.; McQuaid, K. M.; Sames, D. J. Am. Chem. Soc. 2005, 127, 12180.
11. (b) Pastine, S. J.; Sames, D. Org. Lett. 2005, 7, 5429.
12. (c) Tobisu, M.; Chatani, N. Angew. Chem., Int. Ed. 2006, 45, 1683.
13. (d) McQuaid, K. M.; Sames, D. J. Am. Chem. Soc. 2009, 131, 402.
14. (e) Shikanai, D.; Murase, H.; Hata, T.; Urabe, H. J. Am. Chem. Soc. 2009, 131, 3166.
15. (f) Mahoney, S. J.; Moon, D. T.; Hollinger, J.; Fillion, E. Tetrahedron Lett. 2009, 50, 4706.
16. (g) McQuaid, K. M.; Long, J. Z.; Sames, D. Org. Lett. 2009, 11, 2972.
17. (h) Mori, K.; Ohshima, Y.; Ehara, K.; Akiyama, T. Chem. Lett. 2009, 38, 524.
18. For selected examples of 1,5-hydride shift processes in nonconjugated systems, see:(a) Woodward, R. B.; Sondheimer, F.; Mazur, Y. J. Am. Chem. Soc. 1958, 80, 6693.
19. (b) Ten Broeke, J.; Douglas, A. W.; Grabowski, E. J. J. J. Org. Chem. 1976, 41, 3159.
20. (c) Heathcock, C. H. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 14323.
21. (d) Woelfling, J.; Frank, E.; Schneider, G.; Tietze, L. F. Eur. J. Org. Chem. 2004, 90.
22. (e) Cui, L.; Peng, Y.; Zhang, L. J. Am. Chem. Soc. 2009, 131, 8394.
23. For a review on the synthesis of tetrahydroquinolines, see:Katritzky, A. R.; Rachwal, S.; Rachwal, B. Tetrahedron 1996, 52, 15031.
24. For reviews, see:(a) Meth-Cohn, O.; Suschitzky, H. Adv. Heterocycl. Chem. 1972, 14, 211.
25. (b) Verboom, W.; Reinhoudt, D. N. Recl. Trav. Chim. Pays-Bas 1990, 109, 311.
26. (c) Meth-Cohn, O. Adv. Heterocycl. Chem. 1996, 65, 1.
27. (d) Quintela, J. M. Recent Res. Dev. Org. Chem. 2003, 7, 259.
28. (e) Matyus, P.; Elias, O.; Tapolcsanyi, P.; Polonka-Balint, A.; Halasz-Dajka, B. Synthesis 2006, 2625.
29. For selected examples, see:(a) Verboom, W.; Reinhoudt, D. N.; Visser, R.; Harkema, S. J. Org. Chem. 1984, 49, 269.
30. (b) Nijhuis, W. H. N.; Verboom, W.; Reinhoudt, D. N.; Harkema, S. J. Am. Chem. Soc. 1987, 109, 3136.
31. (c) Nijhuis, W. H. N.; Verboom, W.; Abu El-Fadl, A.; Harkema, S.; Reinhoudt, D. N. J. Org. Chem. 1989, 54, 199.
32. (d) Nijhuis, W. H. N.; Verboom, W.; Abu El-Fadl, A.; Van Hummel, G. J.; Reinhoudt, D. N. J. Org. Chem. 1989, 54, 209.
33. (e) De Boeck, B.; Jiang, S.; Janousek, Z.; Viehe, H. G. Tetrahedron 1994, 50, 7075.
34. (f) De Boeck, B.; Janousek, Z.; Viehe, H. G. Tetrahedron 1995, 51, 13239.
35. (g) Ojea, V.; Muinelo, I.; Quintela, J. M. Tetrahedron 1998, 54, 927.
36. (h) Kaval, N.; Halasz-Dajka, B.; Vo-Thanh, G.; Dehaen, W.; Van der Eycken, J.; Matyus, P.; Loupy, A.; Van der Eycken, E. Tetrahedron 2005, 61, 9052.
37. (i) Ruble, J. C.; Hurd, A. R.; Johnson, T. A.; Sherry, D. A.; Barbachyn, M. R.; Toogood, P. L.; Bundy, G. L.; Graber, D. R.; Kamilar, G. M. J. Am. Chem. Soc. 2009, 131, 3991.
38. (a) Zhang, C.; De, C. K.; Mal, R.; Seidel, D. J. Am. Chem. Soc. 2008, 130, 416.
39. (b) Zhang, C.; Murarka, S.; Seidel, D. J. Org. Chem. 2009, 74, 419.
40. (c) Murarka, S.; Zhang, C.; Konieczynska, M. D.; Seidel, D. Org. Lett. 2009, 11, 129.
41. A single nitro group has been shown to be sufficient for activation under thermal conditions:Rabong, C.; Hametner, C.; Mereiter, K.; Kartsev, V. G.; Jordis, U. Heterocycles 2008, 75, 799.
42. For examples of using acyl oxazolidinones as achiral templates, see:(a) Narasaka, K.; Inoue, M.; Okada, N. Chem. Lett. 1986, 1109.
43. (b) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325.
44. (c) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480.
45. (d) Desimoni, G.; Faita, G.; Jorgensen, K. A. Chem. Rev. 2006, 106, 3561.
46. (e) Reymond, S.; Cossy, J. Chem. Rev. 2008, 108, 5359.
47. See the Supporting Information for details.
48. (a) Kanemasa, S.; Oderaotoshi, Y.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Org. Chem. 1997, 62, 6454.
49. (b) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.-i.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074.
50. (c) Iserloh, U.; Curran, D. P.; Kanemasa, S. Tetrahedron: Asymmetry 1999, 10, 2417.
51. (d) Kanemasa, S.; Kanai, T. J. Am. Chem. Soc. 2000, 122, 10710.
52. Reactions performed in toluene, trifluorotoluene, chloroform, dichloromethane, or acetonitrile (all at reflux temperature) led to no formation of product.
53. For additional experiments regarding the interconversion between 5a and 5a′ under the reaction conditions, see the Supporting Information.