Gold and BINOL-phosphoric acid catalyzed enantioselective hydroamination/N-sulfonyliminium cyclization cascade

Organic Letters

Volumn 15, Issue 17, 2013, Pages 4330-4333

  Gregory, Alex W ^a   Jakubec, Pavol ^a   Turner, Paul ^b   Dixon, Darren J ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2,2' DIHYDROXY 1,1' BINAPHTHYL; GOLD; IMINE; NAPHTHOL DERIVATIVE; PHOSPHORIC ACID; SULFONAMIDE;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

AMINATION; CATALYSIS; CYCLIZATION; GOLD; IMINES; MOLECULAR STRUCTURE; NAPHTHOLS; PHOSPHORIC ACIDS; STEREOISOMERISM; SULFONAMIDES;

EID: 84883784457     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol401784h     Document Type: Article

References (84)

1. Hashmi, S. K.; Hubbert, C. Angew. Chem., Int. Ed. 2010, 49, 1010
2. Wang, C.; Han, Z.-Y.; Luo, H.-W.; Gong, L.-Z. Org. Lett. 2010, 12, 2266
3. Liu, X.-Y.; Che, C.-M. Org. Lett. 2009, 11, 4204
4. Rueping, M.; Antonchick, A. P.; Brinkmann, C. Angew. Chem., Int. Ed. 2007, 46, 6903
5. Patil, N. T.; Mutyala, A. K.; Konala, A. K.; Tella, R. B. Chem. Commun. 2012, 48, 3094
6. Liu, X.-Y.; Xiao, Y.-P.; Siu, F.-M.; Ni, L.-C.; Chen, Y.; Wang, L.; Che, C.-M. Org. Biomol. Chem. 2012, 10, 7208
7. Wu, H.; He, Y.-P.; Gong, L.-Z. Adv. Synth. Catal. 2012, 354, 975
8. Cai, Q.; Liang, X.-W.; Wang, S.-G.; Zhang, J.-W.; Zang, X.; You, S.-L. Org. Lett. 2012, 14, 5022
9. Ren, L.; Lei, T.; Ye, J.-X.; Gong, L.-Z. Angew. Chem., Int. Ed. 2012, 51, 771
10. Liu, X.-Y.; Che, C.-M. Org. Lett. 2009, 11, 4204
11. Han, Z.-Y.; Xiao, H.; Chen, X.-H.; Gong, L.-Z. J. Am. Chem. Soc. 2009, 131, 9182
12. Muratore, M. E.; Shi, L.; Pilling, A. W.; Storer, R. I.; Dixon, D. J. Chem. Commun. 2012, 48, 6351
13. Enomoto, T.; Girard, A.-L.; Yasui, Y.; Takemoto, Y. J. Org. Chem. 2009, 74, 9158
14. Cai, Q.; Liu, C.; Liang, X.-W.; You, S.-L. Org. Lett. 2012, 14, 4588
15. Zhang, J.-W.; Xu, Z.; Gu, Q.; Shi, X.-X.; Leng, X.-B.; You, S.-L. Tetrahedron. 2012, 68, 5263
16. Gómez-SanJuan, A.; Sotomayor, N.; Lete, E. Tetrahedron Lett. 2012, 53, 2157
17. Aranzamendi, E.; Sotomayor, N.; Lete, E. J. Org. Chem. 2012, 77, 2986
18. Rueping, M.; Volla, C. M. R.; Bolte, M.; Raabe, G. Adv. Synth. Catal. 2011, 353, 2853
19. Duce, S.; Pesciaioli, F.; Gramigna, L.; Bernard, L.; Mazzanti, A.; Ricci, A.; Bartoli, G.; Bencivennia, G. Adv. Synth. Catal. 2011, 353, 860
20. Rueping, M.; Volla, C. M. R. RSC Adv. 2011, 1, 79
21. Rueping, M.; Raja, S.; Nunez, A. Adv. Synth. Catal. 2011, 353, 563
22. Patil, N. T.; Raut, V. S.; Tella, R. B. Chem. Commun. 2013, 49, 570
23. Wu, H.; He, Y.-P.; Gong, L.-Z. Org. Lett. 2013, 15, 460
24. Courant, T.; Kumarn, S.; He, L.; Retailleau, P.; Masson, G. Adv. Synth. Catal. 2013, 355, 836
25. Cai, Q.; Liang, X.-W.; Wang, S.; You, S.-L. Org. Biomol. Chem. 2013, 11, 1602
26. Aillaud, I.; Barber, D. M.; Thompson, A. L.; Dixon, D. J. Org. Lett. 2013, 15, 2946
27. Cala, L.; Mendoza, A.; Fananas, F. J.; Rodriguez, F. Chem. Commun. 2013, 49, 2715
28. Rueping, M.; Koenigs, R. M.; Atodiresei, I. Chem.-Eur. J. 2010, 16, 9350
29. Shao, A.; Zhang, H. Chem. Soc. Rev. 2009, 38, 2745
30. Parra, A.; Reboredo, S.; Martín Castro, A. M.; Alemán J. Org. Biomol. Chem. 2012, 10, 5001
31. Zhong, C.; Shi, X. Eur. J. Org. Chem. 2010, 16, 2999
32. Loh, C. C. G.; Enders, D. Chem.-Eur. J. 2012, 18, 10212
33. Grondall, C.; Jeanty, M.; Enders, D. Nat. Chem. 2010, 2, 167
34. Du, Z.; Shao, Z. Chem. Soc. Rev. 2013, 42, 1337
35. Muratore, M. E.; Holloway, C. A.; Pilling, A. W.; Storer, I.; Trevitt, G.; Dixon, D. J. J. Am. Chem. Soc. 2009, 131, 10796
36. Holloway, C. A.; Muratore, M. E.; Storer, R. I.; Dixon, D. J. Org. Lett. 2010, 12, 4720
37. Raheem, I. T.; Thiara, P. S.; Peterson, E. A.; Jacobsen, E. N. J. Am. Chem. Soc. 2007, 129, 13404
38. Alemán, J.; Solar, V.; Alvarez-Valdés, A.; Ríos-Luci, C.; Padrón, J. M.; Navarro-Ranninger, C. Med. Chem. Commun. 2011, 2, 789
39. Supuran, C. T.; Scozzafava, A. Exp. Opin. Ther. Pat. 2002, 12, 217
40. Wang, H.-F.; Yang, T.; Xu, P.-F.; Dixon, D. J. Chem. Commun. 2009, 3916
41. Kothandaraman, P.; Rao, W.; Foo, S. J.; Chan, P. W. H. Angew. Chem., Int. Ed. 2010, 49, 4619
42. Cheung, F. K.; Hayes, A. M.; Morris, D. J.; Wills, M. Org. Biomol. Chem. 2007, 5, 1093
43. Barber, D. M.; Sanganee, H.; Dixon, D. J. Chem. Commun. 2011, 47, 4379
44. Barber, D. M.; Sanganee, H. J.; Dixon, D. J. Org. Lett. 2012, 14, 5290
45. Patil, N. T.; Shinde, V. S.; Sridhar, B. Angew. Chem., Int. Ed. 2013, 52, 2251
46. Hashmi, S. K. Chem. Rev. 2007, 107, 3180
47. Li, Z.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239
48. Arcadi, A. Chem. Rev. 2008, 108, 3266
49. Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351
50. Corma, A.; Leyva-Pérez, A.; Sabater, M. J. Chem. Rev. 2011, 111, 1657
51. Rudolph, M.; Hashmi, A. S. K. Chem. Commun. 2011, 47, 6536
52. Hashmi, A. S. K.; Hutchings, G. J. Angew. Chem., Int. Ed. 2006, 45, 7896
53. Toste, F. D. Nature 2007, 446, 395-403
54. Modern Gold Catalyzed Synthesis; Hashmi, A. S. K.; Toste, F. D., Eds.; WILEY-VCH: Weinheim, 2012.
55. Furstner, A. Chem. Soc. Rev. 2009, 38, 3208
56. Rueping, M.; Nachtsteim, B. J.; Ieawsuwan, W.; Atodiresei, I. Angew. Chem., Int. Ed. 2011, 50, 6706
57. Terada, M. Synthesis 2010, 12, 1929
58. Terada, M. Chem. Commun. 2008, 4097
59. Akiyama, T. Chem. Rev. 2007, 107, 5744
60. Akiyama, T.; Itoh, J.; Fuchibe, K. Adv. Synth. Catal. 2006, 348, 999
61. de Vries, J. G.; Mrsic, N. Catal. Sci. Technol. 2011, 1, 727
62. Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 5356
63. Uraguchi, D.; Sorimachi, K.; Terada, M. J. Am. Chem. Soc. 2004, 126, 11804
64. Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem., Int. Ed. 2004, 43, 1566
65. Wang, B.-L.; Zhang, J.-X.; Li, N.-K.; Liu, G.-G.; Shen, Q.; Wang, X.-W. Tetrahedron Lett. 2011, 52, 4671
66. Kang, Q.; Zheng, X.-J.; You, S.-L. Chem.-Eur. J. 2008, 14, 3539
67. Kang, Q.; Zhao, Z.-A.; You, S.-L. J. Am. Chem. Soc. 2007, 129, 1484
68. Chen, L.-Y.; He, H.; Chan, W.-H.; Lee, A. W. M. J. Org. Chem. 2011, 76, 7141
69. Xing, C.-H.; Liao, Y.-X.; Ng, J.; Hu, Q.-S. J. Org. Chem. 2011, 76, 4125
70. Xu, F.; Huang, D.; Han, C.; Shen, W.; Lin, X.; Wang, Y. J. Org. Chem. 2010, 75, 8677
71. Fleischmann, M.; Drettwan, D.; Sugiono, E.; Rueping, M.; Gschwind, R. M. Angew. Chem., Int. Ed. 2011, 50, 6364
72. Bandini, M.; Bottoni, A.; Chiarucci, M.; Cera, G.; Miscione, G. P. J. Am. Chem. Soc. 2012, 134, 20690
73. Nieto-Oberhuber, C.; Lopez, S.; Munoz, M. P.; Cardenas, D. J.; Bunuel, E.; Nevado, C.; Echavarren, A. M. Angew. Chem., Int. Ed. 2005, 44, 6146
74. Perez-Galan, P.; Delpont, N.; Herrero-Gomez, E.; Maseras, F.; Echavarren, A. M. Chem.-Eur. J. 2010, 16, 5324
75. Herrero-Gomez, E.; Nieto-Oberhuber, C.; Lopez, S.; Benet-Buchholz, J.; Echavarren, A. M. Angew. Chem., Int. Ed. 2006, 45, 5455
76. This may be due to its ability to increase tight ion pairing: Brak, K.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2013, 52, 534
77. Schmidbaur, H.; Schier, A. Organometallics 2010, 29, 2
78. Soriano, E.; Marco-Contelles, J. Chem.-Eur. J. 2008, 14, 6771
79. Soriano, E.; Marco-Contelles, J. Acc. Chem. Res. 2009, 42, 1026
80. Li, G.; Zhang, Z.; Zhang, L. J. Am. Chem. Soc. 2008, 130, 3740
81. LaLonde, R. L.; Brenzovich, W. E., Jr.; Benitez, D.; Tkatchouk, E.; Kelley, K.; Goddard, W. A., III; Toste, F. D. Chem. Sci. 2010, 1, 226
82. Liu, L.; Hammond, G. B. Chem. Soc. Rev. 2012, 41, 3129
83. We cannot rule out Lewis acid assisted Brønsted acid catalysis: Yang, T.; Campbell, L.; Dixon, D. J. J. Am. Chem. Soc. 2007, 129, 12070
84. Raducan, M.; Moreno, M.; Boura, C.; Echavarren, A. M. Chem. Commun. 2012, 48, 52