Shedding light on organocatalysis - Light-assisted asymmetric ion-pair catalysis for the enantioselective hydrogenation of pyrylium ions

Chemistry - A European Journal

Volumn 19, Issue 30, 2013, Pages 9775-9779

  Hsiao, Chien Chi ^a   Liao, Hsuan Hung ^a   Sugiono, Erli ^a   Atodiresei, Iuliana ^a   Rueping, Magnus ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

asymmetric catalysis; benzopyrane; chiral ion pair; oxocarbenium ion; reduction

Indexed keywords

ASYMMETRIC CATALYSIS; BENZOPYRANE; ENANTIOSELECTIVE HYDROGENATION; ION PAIRS; ORGANOCATALYSIS; OXOCARBENIUM; PHOTO-ASSISTED; SHEDDING LIGHT;

CATALYSIS; ENANTIOSELECTIVITY; HYDROGENATION; REACTION KINETICS; REDUCTION;

IONS;

EID: 84880276893     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201300766     Document Type: Article

References (98)

1. L. F. Tietze, Chem. Rev. 1996, 96, 115-136
2. L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137-170
3. Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163
4. L. F. Tietze, G. Brasche, K. M. Gericke, in Domino Reactions in Organic Synthesis, Wiley-VCH, Weinheim, 2006.
5. P. N. Moquist, T. Kodama, S. E. Schaus, Angew. Chem. 2010, 122, 7250-7254
6. Angew. Chem. Int. Ed. 2010, 49, 7096-7100
7. F. Benfatti, E. Benedetto, P. G. Cozzi, Chem. Asian J. 2010, 5, 2047-2052
8. M. Rueping, C. M. R. Volla, I. Atodiresei, Org. Lett. 2012, 14, 4642-4645.
9. G. P. Ellis, I. M. Lockhart, in The Chemistry of Heterocyclic Compounds, Chromenes, Chromanones, and Chromones, Vol. 31 (Ed.:, G. P. Ellis,), Wiley-VCH, Weinheim, 2007, pp. 1-1196
10. R. D. H. Murray, J. Medez, S. A. Brown, in The Natural Coumarins: Occurrence, Chemistry and Biochemistry Wiley, New York, 1982.
11. T. Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2006, 348, 999-1010
12. T. Akiyama, Chem. Rev. 2007, 107, 5744-5758
13. M. Terada, Chem. Commun. 2008, 4097-4112
14. D. Kampen, C. Reisinger, B. List, Top. Curr. Chem. 2009, 291, 395-456
15. H. Yamamoto, N. Payette, in Hydrogen Bonding in Organic Synthesis (Ed.:, P. M. Pihko,), Wiley-VCH, Weinheim, 2009, pp. 73-140
16. M. Terada, Synthesis 2010, 1929-1982
17. S. Schenker, A. Zamfir, M. Freund, S. B. Tsogoeva, Eur. J. Org. Chem. 2011, 2209-2222
18. M. Terada, Curr. Org. Chem. 2011, 15, 2227-2256
19. M. Rueping, A. Kuenkel, I. Atodiresei, Chem. Soc. Rev. 2011, 40, 4539-4549. Recent examples from our group
20. M. Fleischmann, D. Drettwan, E. Sugiono, M. Rueping, R. M. Gschwind, Angew. Chem. 2011, 123, 6488-6493
21. Angew. Chem. Int. Ed. 2011, 50, 6364-6369
22. M. Rueping, C. M. R. Volla, RSC Adv. 2011, 1, 79-82
23. M. Rueping, L. Hubener, Synlett 2011, 1243-1246
24. M. Rueping, A. P. Antonchick, Angew. Chem. 2008, 120, 10244-10247
25. Angew. Chem. Int. Ed. 2008, 47, 10090-10093
26. M. Rueping, T. Theissmann, Chem. Sci. 2010, 1, 473-476
27. M. Rueping, T. Bootwicha, S. Kambutong, E. Sugiono, Chem. Asian J. 2012, 7, 1195-1198.
28. D. Nakashima, H. Yamamoto, J. Am. Chem. Soc. 2006, 128, 9626-9627. Reviews
29. C. H. Cheon, H. Yamamoto, Chem. Commun. 2011, 47, 3043-3056
30. M. Rueping, B. J. Nachtsheim, W. Ieawsuwan, I. Atodiresei, Angew. Chem. 2011, 123, 6838-6853
31. Angew. Chem. Int. Ed. 2011, 50, 6706-6720. for further examples, see
32. M. Rueping, W. Ieawsuwan, A. P. Antonchick, B. J. Nachtsheim, Angew. Chem. 2007, 119, 2143-2146
33. Angew. Chem. Int. Ed. 2007, 46, 2097-2100
34. M. Rueping, B. J. Nachtsheim, S. A. Moreth, M. Bolte, Angew. Chem. 2008, 120, 603-606
35. Angew. Chem. Int. Ed. 2008, 47, 593-596
36. D. Enders, A. A. Narine, F. Toulgoat, T. Bisschops, Angew. Chem. 2008, 120, 5744-5748
37. Angew. Chem. Int. Ed. 2008, 47, 5661-5665
38. M. Rueping, T. Theissmann, A. Kuenkel, R. M. Koenigs, Angew. Chem. 2008, 120, 6903-6906
39. Angew. Chem. Int. Ed. 2008, 47, 6798-6801
40. M. Rueping, W. Ieawsuwan, Adv. Synth. Catal. 2009, 351, 78-84
41. M. Zeng, Q. Kang, Q.-L. He, S.-L. You, Adv. Synth. Catal. 2008, 350, 2169-2173
42. M. Rueping, M.-Y. Lin, Chem. Eur. J. 2010, 16, 4169-4172
43. M. Rueping, B. J. Nachtsheim, R. M. Koenigs, W. Ieawsuwan, Chem. Eur. J. 2010, 16, 13116-13126
44. M. Rueping, B. J. Nachtsheim, Synlett 2010, 119-122
45. M. Rueping, E. Merino, R. M. Koenigs, Adv. Synth. Catal. 2010, 352, 2629-2634
46. C. H. Cheon, H. Yamamoto, Org. Lett. 2010, 12, 2476-2479
47. M. Rueping, U. Uria, M.-Y. Lin, I. Atodiresei, J. Am. Chem. Soc. 2011, 133, 3732-3735
48. T. Hashimoto, H. Nakatsu, K. Yamamoto, K. Maruoka, J. Am. Chem. Soc. 2011, 133, 9730-9733
49. M. Rueping, R. M. Koenigs, Chem. Commun. 2011, 47, 304-306
50. M. Rueping, W. Ieawsuwan, Chem. Commun. 2011, 47, 11450-11452
51. S. Raja, W. Ieawsuwan, V. Korotkov, M. Rueping, Chem. Asian J. 2012, 7, 2361-2366
52. M. Rueping, M. S. Maji, H. B. Küçük, I. Atodiresei, Angew. Chem. 2012, 124, 13036-13040
53. Angew. Chem. Int. Ed. 2012, 51, 12864-12868.
54. S. E. Reisman, A. G. Doyle, E. N. Jacobsen, J. Am. Chem. Soc. 2008, 130, 7198-7199
55. M. Terada, H. Tanaka, K. Sorimachi, J. Am. Chem. Soc. 2009, 131, 3430-3431
56. Q.-W. Zhang, C.-A. Fan, H.-J. Zhang, Y.-Q. Tu, Y.-M. Zhao, P. Gu, Z.-M. Chen, Angew. Chem. 2009, 121, 8724-8726
57. Angew. Chem. Int. Ed. 2009, 48, 8572-8574
58. I. Čoric̈, S. Vellalath, B. List, J. Am. Chem. Soc. 2010, 132, 8536-8537
59. I. Čoric̈, S. Müller, B. List, J. Am. Chem. Soc. 2010, 132, 17370-17373
60. I. Čoric̈, B. List, Nature 2012, 483, 315-319
61. Z. Sun, G. A. Winschel, A. Borovika, P. Nagorny, J. Am. Chem. Soc. 2012, 134, 8074-8077
62. B. Guo, G. Schwarzwalder, J. T. Njardason, Angew. Chem. 2012, 124, 5773-5776
63. Angew. Chem. Int. Ed. 2012, 51, 5675-5678.
64. J. Lacour, V. Hebbe-Viton, Chem. Soc. Rev. 2003, 32, 373-382
65. J. Lacour, D. Moraleda, Chem. Commun. 2009, 7073-7089
66. R. J. Phipps, G. L. Hamilton, F. D. Toste, Nat. Chem. 2012, 4, 603-614.
67. For kinetics of the reaction/reduction of benzopyrilium ions:, C. Fichtner, G. Remennikov, H. Mayr, Eur. J. Org. Chem. 2001, 4451-4456.
68. S.-L. You, Chem. Asian J. 2007, 2, 820-827
69. M. Rueping, E. Sugiono, F. R. Schoepke, Synlett 2010, 852-865
70. M. Rueping, J. Dufour, F. R. Schoepke, Green Chem. 2011, 13, 1084-1105
71. C. Zheng, S.-L. You, Chem. Soc. Rev. 2012, 41, 2498-2518. For an important study on the hydride-donor abilities of HEH see
72. D. Richter, H. Mayr, Angew. Chem. 2009, 121, 1992-1995
73. Angew. Chem. Int. Ed. 2009, 48, 1958-1961
74. X.-Q. Zhu, M.-T. Zhang, A. Yu, C.-H. Wang, J.-P. Cheng, J. Am. Chem. Soc. 2008, 130, 2501-2516.
75. D. Dewar, R. G. Sutherland, J. Chem. Soc. D. 1970, 272-273
76. R. Matsushima, M. Suzuki, Bull. Chem. Soc. Jpn. 1992, 65, 39-45
77. H. Horiuchi, H. Shirase, T. Okutsu, R. Matsushima, H. Hiratsuka, Chem. Lett. 2000, 29, 96-97.
78. B. E. Norcross, P. E. Klinedinst, F. H. Westheimer, J. Am. Chem. Soc. 1962, 84, 797-802
79. Y. Inoue, S. Imaizumi, H. Itoh, T. Shinya, H. Hashimoto, S. Miyano, Bull. Chem. Soc. Jpn. 1988, 61, 3020-3022
80. Y. Ohnishi, M. Kagami, A. Ohno, Chem. Lett. 1975, 4, 125-128
81. X.-Q. Zhu, H.-R. Li, Q. Li, T. Ai, J.-Y. Lu, Y. Yang, J.-P. Cheng, Chem. Eur. J. 2003, 9, 871-880
82. V. V. De Rosso, F. E. Morán Vieyra, A. Z. Mercadante, C. D. Borsarelli, Free Radical Res. 2008, 42, 885-891.
83. M. Kotke, P. R. Schreiner, Tetrahedron 2006, 62, 434-439
84. Kotke, Mike (Ph. D. thesis 2009, http://geb.uni-giessen.de/geb/volltexte/ 2010/7835/)
85. Z. Zhang, P. R. Schreiner, Chem. Soc. Rev. 2009, 38, 1187-1198.
86. A very interesting example of silyl ester/phosphate ion pair in asymmetric anion pair catalysis:, M. Sickert, C. Schneider, Angew. Chem. 2008, 120, 3687-3690
87. Angew. Chem. Int. Ed. 2008, 47, 3631-3634.
88. Y. Inoue, Chem. Rev. 1992, 92, 741-770
89. A. G. Griesbeck, U. J. Meierhenrich, Angew. Chem. 2002, 114, 3279-3286
90. Angew. Chem. Int. Ed. 2002, 41, 3147-3154
91. J. Iriondo-Alberdi, M. F. Greany, Eur. J. Org. Chem. 2007, 4801-4815
92. J. R. Scheffer, W. Xia, Top. Curr. Chem. 2005, 254, 233-262
93. C. Yang, W. Xia, Chem. Asian J. 2009, 4, 1774-1784
94. T. Bach, J. P. Hehn, Angew. Chem. 2011, 123, 1032-1077
95. Angew. Chem. Int. Ed. 2011, 50, 1000-1045.
96. E. Marqués-Lõpez, R. P. Herrera, M. Christmann, Nat. Prod. Rep. 2010, 27, 1138-1167
97. R. Marcia de Figueiredo, M. Christmann, Eur. J. Org. Chem. 2007, 2575-2600.
98. D. Avnir, E. Weller, M. Ottolenghi, J. Am. Chem. Soc. 1989, 111, 2001-2003.