A cooperative hydrogen-bond-promoted organophotoredox catalysis strategy for highly diastereoselective, reductive enone cyclization

Chemistry - A European Journal

Volumn 19, Issue 22, 2013, Pages 6950-6955

  Neumann, Matthias ^a   Zeitler, Kirsten ^a,b  

^a UNIVERSITY OF REGENSBURG   (Germany)

^b UNIVERSITY OF LEIPZIG   (Germany)

Author keywords

organocatalysis; photocatalysis; redox chemistry; reductive cyclization; thiourea

Indexed keywords

DIASTEREOSELECTIVE; HETEROCYCLES; ORGANOCATALYSIS; ORGANOCATALYTIC; REDOX CHEMISTRY; REDUCTIVE CYCLIZATION;

HYDROGEN; PHOTOCATALYSIS; REACTION KINETICS; STEREOSELECTIVITY; THIOUREAS;

CYCLIZATION;

EID: 84878107052     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201204573     Document Type: Article

References (80)

1. R. C. Wende, P. Schreiner, Green Chem. 2012, 14, 1821
2. A. E. Allen, D. W. C. MacMillan, Chem. Sci. 2012, 3, 633
3. C. Grondal, M. Jeanty, D. Enders, Nat. Chem. 2010, 2, 167
4. Ł. Albrecht, H. Jiang, K. A. Jørgensen, Angew. Chem. 2011, 123, 8642
5. Angew. Chem. Int. Ed. 2011, 50, 8492.
6. S. B. Jones, B. Simmons, A. Mastracchio, D. W. C. MacMillan, Nature 2011, 475, 183
7. D. W. C. MacMillan, Nature 2008, 455, 304.
8. D. Kalyani, K. B. McMurtrey, S. R. Neufeldt, M. S. Sanford, J. Am. Chem. Soc. 2011, 133, 18566
9. M. Rueping, R. M. Koenigs, K. Poscharny, D. C. Fabry, D. Leonori, C. Vila, Chem. Eur. J. 2012, 18, 5170
10. Y. Ye, M. S. Sanford, J. Am. Chem. Soc. 2012, 134, 9034
11. S. Zhu, M. Rueping, Chem. Commun. 2012, 48, 11960.
12. D. A. Nicewicz, D. W. C. MacMillan, Science 2008, 322, 77.
13. M. Rueping, C. Vila, R. M. Koenigs, K. Poscharny, D. C. Fabry, Chem. Commun. 2011, 47, 2360; for the cooperative combination of metal-oxide photoredox catalysis with enamine catalysis, see
14. M. Rueping, J. Zoller, D. C. Fabry, K. Poscharny, R. M. Koenigs, T. E. Weirich, J. Mayer, Chem. Eur. J. 2012, 18, 3478.
15. D. A. DiRocco, T. Rovis, J. Am. Chem. Soc. 2012, 134, 8094.
16. For a recent application of Cu-based photoredox catalysts, see:, M. Pirtsch, S. Paria, T. Matsuno, H. Isobe, O. Reiser, Chem. Eur. J. 2012, 18, 7336.
17. M. Neumann, S. Füldner, B. König, K. Zeitler, Angew. Chem. 2011, 123, 981
18. Angew. Chem. Int. Ed. 2011, 50, 951; for an overview on other applications of metal-free photocatalysis, see
19. D. Ravelli, M. Fagnoni, A. Albini, Chem. Soc. Rev. 2013, 42, 97
20. D. Ravelli, M. Fagnoni, ChemCatChem 2012, 4, 169; for further examples, see
21. Y. Pan, C. W. Kee, L. Chen, C.-H. Tan, Green Chem. 2011, 13, 2682
22. Y. Pan, S. Wang, C. W. Kee, E. Dubuisson, Y. Yang, K. P. Loh, C.-H. Tan, Green Chem. 2011, 13, 3341
23. D. P. Hari, B. König, Org. Lett. 2011, 13, 3852
24. D. P. Hari, P. Schroll, B. König, J. Am. Chem. Soc. 2012, 134, 2958
25. P. Schroll, D. P. Hari, B. König, ChemistryOpen 2012, 1, 130
26. K. Fidaly, C. Ceballos, A. Falguieres, M. S.-I. Veitia, A. Guy, C. Ferroud, Green Chem. 2012, 14, 1293
27. Y. C. Teo, Y. Pan, C. H. Tan, ChemCatChem 2013, 5, 235
28. D. P. Hari, T. Hering, B. König, Org. Lett. 2012, 14, 5334
29. D. S. Hamilton, D. A. Nicewicz, J. Am. Chem. Soc. 2012, 134, 18577.
30. A. G. Doyle, E. N. Jacobsen, Chem. Rev. 2007, 107, 5713
31. P. M. Pihko, Angew. Chem. 2004, 116, 2110
32. Angew. Chem. Int. Ed. 2004, 43, 2062
33. P. R. Schreiner, Chem. Soc. Rev. 2003, 32, 289
34. M. S. Taylor, E. N. Jacobsen, Angew. Chem. 2006, 118, 1550
35. Angew. Chem. Int. Ed. 2006, 45, 1520.
36. A. Bauer, F. Westkämper, S. Grimme, T. Bach, Nature 2005, 436, 1139
37. C. Müller, T. Bach, Aust. J. Chem. 2008, 61, 557.
38. D. Seebach, Angew. Chem. 1979, 91, 259
39. Angew. Chem. Int. Ed. Engl. 1979, 18, 239
40. X. Bugaut, F. Glorius, Chem. Soc. Rev. 2012, 41, 3511.
41. E. J. Enholm, K. S. Kinter, J. Am. Chem. Soc. 1991, 113, 7784
42. D. S. Hays, G. C. Fu, J. Org. Chem. 1996, 61, 4
43. for an anionic radical-chain cyclobutanation initiated by low concentration of Gilman cuprates, see:, J. Yang, D. F. Cauble, A. J. Berro, N. L. Bauld, M. J. Krische, J. Org. Chem. 2004, 69, 7979.
44. J. Montgomery, E. Oblinger, A. V. Savchenko, J. Am. Chem. Soc. 1997, 119, 4911
45. T.-G. Baik, A. L. Luis, L.-C. Wang, M. J. Krische, J. Am. Chem. Soc. 2001, 123, 6716
46. A. D. Jenkins, A. Herath, M. Song, J. Montgomery, J. Am. Chem. Soc. 2011, 133, 14460.
47. J. Yang, G. A. N. Felton, N. L. Bauld, M. J. Krische, J. Am. Chem. Soc. 2004, 126, 1634.
48. G. A. N. Felton, N. L. Bauld, Tetrahedron 2004, 60, 10999
49. Y. Roh, H.-Y. Jang, V. Lynch, N. L. Bauld, M. J. Krische, Org. Lett. 2002, 4, 611.
50. G. Pandey, S. Hajra, Angew. Chem. 1994, 106, 1217
51. Angew. Chem. Int. Ed. Engl. 1994, 33, 1169
52. G. Pandey, S. Hajra, M. K. Ghorai, Tetrahedron Lett. 1994, 35, 7837
53. G. Pandey, S. Hajra, M. K. Ghorai, K. R. Kumar, J. Am. Chem. Soc. 1997, 119, 8777.
54. M. A. Ischay, M. E. Anzovino, J. Du, T. P. Yoon, J. Am. Chem. Soc. 2008, 130, 12886
55. J. Du, T. P. Yoon, J. Am. Chem. Soc. 2009, 131, 14604
56. J. Du, L. R. Espelt, I. A. Guzei, T. P. Yoon, Chem. Sci. 2011, 2, 2115.
57. Compared with experiments done by Yoon and co-workers (23W fluorescent bulb or green LEDs instead of a 275W sunlight lamp with a considerable percentage of UV irradiation), our conditions resulted in longer reaction times (14h vs. 1h). We assume this to be responsible for obtaining the alternative relative stereochemistry. For the spectral distribution of a 275W sunlight lamp (GE), see:, T. P. Dryja, G. P. Kimball, D. M. Albert, Invest. Ophthalmol. Visual Sci. 1980, 19, 559.
58. H. Du, D. Zhao, K. Ding, Chem. Eur. J. 2004, 10, 5964
59. Y. Huang, A. K. Unni, A. N. Thadani, V. H. Rawal, Nature 2003, 424, 146
60. A. N. Thadani, A. R. Stankovic, V. H. Rawal, Proc. Natl. Acad. Sci. USA 2004, 101, 5846
61. D. Seebach, A. K. Beck, H.-U. Bichsel, A. Pichota, C. Sparr, R. Wünsch, W. B. Schweizer, Helv. Chim. Acta 2012, 95, 1303.
62. M. Kotke, P. R. Schreiner, Tetrahedron 2006, 62, 434
63. M. Kotke, P. R. Schreiner, Synthesis 2007, 779
64. P. R. Schreiner, A. Wittkopp, Org. Lett. 2002, 4, 217
65. A. Wittkopp, P. R. Schreiner, Chem. Eur. J. 2003, 9, 407
66. G. Jakab, C. Tancon, Z. Zhang, K. M. Lippert, P. R. Schreiner, Org. Lett. 2012, 14, 1724.
67. L. Furst, B. S. Matsuura, J. M. R. Narayanam, J. W. Tucker, C. R. J. Stephenson, Org. Lett. 2010, 12, 3104.
68. M.-H. Larraufie, R. Pellet, L. Fensterbank, J.-P. Goddard, E. Lacôte, M. Malacria, C. Ollivier, Angew. Chem. 2011, 123, 4555
69. Angew. Chem. Int. Ed. 2011, 50, 4463.
70. H. O. House, L. E. Huber, M. J. Umen, J. Am. Chem. Soc. 1972, 94, 8471.
71. L. Flamigni, A. Barbieri, C. Sabatini, B. Ventura, F. Barigelletti, Top. Curr. Chem. 2007, 281, 143.
72. J. E. Baldwin, J. Chem. Soc. Chem. Commun. 1976, 734.
73. P. M. Brown, N. Käppel, P. J. Murphy, S. J. Coles, M. B. Hursthouse, Tetrahedron 2007, 63, 1100
74. L.-C. Wang, A. L. Luis, K. Agapiou, H.-Y. Jang, M. J. Krische, J. Am. Chem. Soc. 2002, 124, 2402
75. P. S. Selig, S. J. Miller, Tetrahedron Lett. 2011, 52, 2148.
76. For an early example of trapping α-keto radicals with allyltributyltin, see:, E. Hasegawa, K. Ishiyama, T. Kato, T. Horaguchi, T. Shimizu, S. Tanaka, Y. Yamashita, J. Org. Chem. 1992, 57, 5352.
77. H.-W. Shih, M. N. VanderWal, R. L. Grange, D. W. C. MacMillan, J. Am. Chem. Soc. 2010, 132, 13600
78. J. D. Nguyen, E. M. D'Amato, J. M. R. Narayanam, C. R. J. Stephenson, Nat. Chem. 2012, 4, 854
79. I. M. Dixon, J.-P. Collin, J.-P. Sauvage, L. Flamigni, S. Encinas, F. Barigelletti, Chem. Soc. Rev. 2000, 29, 385.
80. Initial efforts to induce enantioselectivity by using chiral thiourea catalysts were unsuccessful.