Regio- and Enantioselective Synthesis of N-Substituted Pyrazoles by Rhodium-Catalyzed Asymmetric Addition to Allenes

Angewandte Chemie - International Edition

Volumn 54, Issue 24, 2015, Pages 7149-7153

  Haydl, Alexander M ^a   Xu, Kun ^a   Breit, Bernhard ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

Author keywords

allenes; allylic compounds; asymmetric catalysis; heterocycles; rhodium

Indexed keywords

CATALYSIS; FUNCTIONAL GROUPS; HYDROCARBONS; RHODIUM;

ALLENES; ALLYLIC COMPOUNDS; ASYMMETRIC ADDITION; ASYMMETRIC CATALYSIS; ENANTIOSELECTIVE SYNTHESIS; HETEROCYCLES; PYRAZOLE DERIVATIVES; SUBSTITUTED PYRAZOLES;

RHODIUM COMPOUNDS;

ALKADIENE; NITROGEN; PROPADIENE; PYRAZOLE; PYRAZOLE DERIVATIVE; RHODIUM; RUXOLITINIB;

CATALYSIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKADIENES; CATALYSIS; NITROGEN; PYRAZOLES; RHODIUM; STEREOISOMERISM;

EID: 84930615780     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201501758     Document Type: Article

References (79)

1. J. C. Byrd, et al., N. Engl. J. Med. 2013, 369, 32-42
2. A. Turetsky, E. Kim, R. H. Kohler, M. A. Miller, R. Weissleder, Sci. Rep. 2014, 4, 1-7.
3. S. Verstovsek, et al., N. Engl. J. Med. 2012, 366, 799-807
4. R. A. Mesa, U. Yasothan, P. Kirkpatrick, Nat. Rev. Drug Discovery 2012, 11, 103-104
5. P. Koppikar, et al., Nature 2012, 489, 155-159.
6. A. Guzman-Perez, et al., Bioorg. Med. Chem. Lett. 2013, 23, 3051-3058
7. Y. Xiong, et al., J. Med. Chem. 2012, 55, 6137-6148.
8. F. Roussi, A. Chauveau, M. Bonin, L. Micouin, H.-P. Husson, Synthesis 2000, 1170-1179
9. C. M. Park, D. J. Jeon, Org. Biomol. Chem. 2012, 10, 2613-2620
10. A. V. Kurkin, A. A. Utkina, M. A. Yurovskaya, Chem. Heterocycl. Compd. 2008, 44, 106-108
11. J.-J. Wen, H.-T. Tang, K. Xiong, Z.-C. Ding, Z.-P. Zhan, Org. Lett. 2014, 16, 5940-5943.
12. C. W. Zapf, B. S. Gerstenberger, L. Xing, D. C. Limburg, D. R. Anderson, N. Caspers, S. Han, A. Aulabaugh, R. Kurumbail, S. Shakya, X. Li, V. Spaulding, R. M. Czerwinski, N. Seth, Q. G. Medley, J. Med. Chem. 2012, 55, 10047-10063
13. A. A. Zabierek, K. M. Konrad, A. M. Haidle, Tetrahedron Lett. 2008, 49, 2996-2998
14. J. Comas-Barceló, R. S. Foster, B. Fiser, E. Gomez-Bengoa, J. P. A. Harrity, Chem. Eur. J. 2015, 21, 3257-3263.
15. S. A. Popov, Y. V. Gatilov, T. V. Rybalova, O. A. Kholdeeva, A. V. Tkachev, Tetrahedron: Asymmetry 2001, 12, 2875-2881
16. P. Li, F. Fang, J. Cheng, J. Wang, Tetrahedron: Asymmetry 2014, 25, 98-101
17. A. G. Algarra, D. L. Davies, Q. Khamker, S. A. Macgregor, C. L. McMullin, K. Singh, B. Villa-Marcos, Chem. Eur. J. 2015, 21, 3087-3096
18. S. Gogoi, C.-G. Zhao, D. Ding, Org. Lett. 2009, 11, 2249-2252
19. Q. Lin, D. Meloni, Y. Pan, M. Xia, J. Rodgers, S. Shepard, M. Li, L. Galya, B. Metcalf, T.-Y. Yue, P. Liu, J. Zhou, Org. Lett. 2009, 11, 1999-2002.
20. N. Nishina, Y. Yamamoto, Angew. Chem. Int. Ed. 2006, 45, 3314-3317
21. Angew. Chem. 2006, 118, 3392-3395
22. R. L. Lalonde, B. D. Sherry, E. J. Kang, F. D. Toste, J. Am. Chem. Soc. 2007, 129, 2452-2453
23. Z. Zhang, C. F. Bender, R. A. Widenhoefer, J. Am. Chem. Soc. 2007, 129, 14148-14149
24. N. D. Shapiro, V. Rauniyar, G. L. Hamilton, J. Wu, F. D. Toste, Nature 2011, 470, 245-250
25. K. L. Butler, M. Tragni, R. A. Widenhoefer, Angew. Chem. Int. Ed. 2012, 51, 5175-5178
26. Angew. Chem. 2012, 124, 5265-5268
27. L. I. Rodríguez, T. Roth, J. L. Fillol, H. Wadepohl, L. H. Gade, Chem. Eur. J. 2012, 18, 3721-3728
28. C. Michon, F. Medina, M.-A. Abadie, F. Agbossou-Niedercorn, Organometallics 2013, 32, 5589-5600.
29. P. Koschker, A. Lumbroso, B. Breit, J. Am. Chem. Soc. 2011, 133, 20746-20749
30. M. L. Cooke, K. Xu, B. Breit, Angew. Chem. Int. Ed. 2012, 51, 10876-10879
31. Angew. Chem. 2012, 124, 11034-11037
32. K. Xu, N. Thieme, B. Breit, Angew. Chem. Int. Ed. 2014, 53, 2162-2165
33. Angew. Chem. 2014, 126, 2194-2197
34. K. Xu, N. Thieme, B. Breit, Angew. Chem. Int. Ed. 2014, 53, 7268-7271
35. Angew. Chem. 2014, 126, 7396-7399
36. C. Li, B. Breit, J. Am. Chem. Soc. 2014, 136, 862-865
37. C. Li, M. Kähny, B. Breit, Angew. Chem. Int. Ed. 2014, 53, 13780-13784
38. Angew. Chem. 2014, 126, 14000-14004
39. A. B. Pritzius, B. Breit, Angew. Chem. Int. Ed. 2015, 54, 3121-3125
40. A. B. Pritzius, B. Breit, Angew. Chem. 2015, 127, 3164-3168.
41. R. Zimmer, C. Dinesh, E. Nandanan, A. F. Khan, Chem. Rev. 2000, 100, 3067-3125
42. I. S. Kim, M. J. Krische, Org. Lett. 2008, 10, 513-515
43. T. Kawamoto, S. Hirabayashi, X. Guo, T. Nishimura, T. Hayashi, Chem. Commun. 2009, 3528-3530
44. J. Moran, A. Preetz, R. A. Mesch, M. J. Krische, Nat. Chem. 2011, 3, 287-290.
45. B. M. Trost, W. Brieden, Angew. Chem. Int. Ed. Engl. 1992, 31, 1335-1336
46. Angew. Chem. 1992, 104, 1392-1394
47. L. M. Lutete, I. Kadota, Y. Yamamoto, J. Am. Chem. Soc. 2004, 126, 1622-1623
48. A. Lumbroso, P. Koschker, N. R. Vautravers, B. Breit, J. Am. Chem. Soc. 2011, 133, 2386-2389
49. A. Lumbroso, N. Abermil, B. Breit, Chem. Sci. 2012, 3, 789-793.
50. B. M. Trost, Chem. Rev. 1996, 96, 395-422
51. B. M. Trost, M. L. Crawley, Chem. Rev. 2003, 103, 2921-2943
52. Z. Lu, S. Ma, Angew. Chem. Int. Ed. 2008, 47, 258-297
53. Angew. Chem. 2008, 120, 264-303
54. D. C. Vrieze, G. S. Hoge, P. Z. Hoerter, J. T. Van Haitsma, B. M. Samas, Org. Lett. 2009, 11, 3140-3142
55. T. Hayashi, A. Okada, T. Suzuka, M. Kawatsura, Org. Lett. 2003, 5, 1713-1715
56. P. A. Evans, D. K. Leahy, J. Am. Chem. Soc. 2002, 124, 7882-7883.
57. G. Liu, Y. Wu, Top. Curr. Chem. 2010, 292, 195-209
58. M. S. Chen, M. C. White, J. Am. Chem. Soc. 2004, 126, 1346-1347
59. G. Liu, S. S. Stahl, J. Am. Chem. Soc. 2007, 129, 6328-6335
60. G. Yin, Y. Wu, G. Liu, J. Am. Chem. Soc. 2010, 132, 11978-11987.
61. J. L. G. De Paz, J. Elguero, C. Foces-Foces, A. L. Llamas-Saiz, F. Aguilar-Parrilla, O. Klein, H.-H. Limbach, J. Chem. Soc. Perkin Trans. 2 1997, 101-109
62. S. Trofimenko, G. P. A. Yap, F. A. Jove, R. M. Claramunt, M. A. García, M. D. S. Maria, I. Alkorta, J. Elguero, Tetrahedron 2007, 63, 8104-8111
63. P. Cornago, R. M. Claramunt, L. Bouissane, J. Elguero, Tetrahedron 2008, 64, 3667-3673
64. M. Á. García, P. Cabildo, R. M. Claramunt, E. Pinilla, M. R. Torres, I. Alkorta, J. Elguero, Inorg. Chim. Acta 2010, 363, 1332-1342.
65. G. Xu, S. R. Gilbertson, Org. Lett. 2005, 7, 4605-4608
66. B. Bhayana, B. P. Fors, S. L. Buchwald, Org. Lett. 2009, 11, 3954-3957
67. R. S. Foster, H. Adams, H. Jakobi, J. P. A. Harrity, J. Org. Chem. 2013, 78, 4049-4064
68. C.-P. Zhang, D. A. Vicic, Chem. Asian J. 2012, 7, 1756-1758.
69. B. Breit, Angew. Chem. Int. Ed. 2005, 44, 6816-6825
70. Angew. Chem. 2005, 117, 6976-6986
71. B. Breit, W. Seiche, J. Am. Chem. Soc. 2003, 125, 6608-6609
72. U. Gellrich, W. Seiche, M. Keller, B. Breit, Angew. Chem. Int. Ed. 2012, 51, 11033-11038
73. Angew. Chem. 2012, 124, 11195-11200
74. V. Agabekov, W. Seiche, B. Breit, Chem. Sci. 2013, 4, 2418-2422.
75. J. U. Rhee, M. J. Krische, J. Am. Chem. Soc. 2006, 128, 10674-10675
76. G. A. Cortez, R. R. Schrock, A. H. Hoveyda, Angew. Chem. Int. Ed. 2007, 46, 4534-4538
77. Angew. Chem. 2007, 119, 4618-4622
78. P. D. Williams, D. Perlow, L. S. Payne, K. M. Holloway, P. K. Siegl, J. Med. Chem. 1991, 34, 887-900
79. R. A. Khera, A. Ali, M. Hussain, J. Tatar, A. Villinger, P. Langer, Synlett 2010, 13, 1923-1926.