One-Pot asymmetric nitro-mannich/hydroamination cascades for the synthesis of pyrrolidine derivatives: Combining organocatalysis and gold catalysis

ACS Catalysis

Volumn 4, Issue 2, 2014, Pages 634-638

  Barber, David M ^a   Ďuriš, Andrej ^a   Thompson, Amber L ^a   Sanganee, Hitesh J ^b   Dixon, Darren J ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

cascade reactions; gold catalysis; hydroamination; nitro Mannich; organocatalysis; pyrrolidine

Indexed keywords

CASCADE REACTIONS; GOLD CATALYSIS; HYDROAMINATIONS; NITRO-MANNICH; ORGANOCATALYSIS; PYRROLIDINES;

ENANTIOSELECTIVITY; GOLD; RATE CONSTANTS; REACTION KINETICS;

CATALYSIS;

EID: 84893853683     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/cs401008v     Document Type: Article

References (74)

1. Fattorusso, E.; Taglialatela-Scafati, O. Modern Alkaloids: Structure, Isolation, Synthesis, Biology; Wiley-VCH: Weinheim, 2007.
2. Michael, J. P. Nat. Prod. Rep. 2008, 25, 139-165
3. Royer, J.; Bonin, M.; Micouin, L. Chem. Rev. 2004, 104, 2311-2352
4. Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127-2198
5. Pandey, G.; Banerjee, P.; Gadre, S. R. Chem. Rev. 2006, 106, 4484-4517
6. Gärtner, M.; Weihofen, R.; Helmchen, G. Chem.-Eur. J. 2011, 17, 7605-7622
7. Kumar, I.; Mir, N. A.; Gupta, V. K.; Rajnikant Chem. Commun. 2012, 48, 6975-6977
8. Cheng, T.; Meng, S.; Huang, Y. Org. Lett. 2013, 15, 1958-1961
9. Jean, A.; Blanchet, J.; Rouden, J.; Maddaluno, J.; De Paolis, M. Chem. Commun. 2013, 49, 1651-1653
10. Trost, B. M.; Lam, T. M.; Herbage, M. A. J. Am. Chem. Soc. 2013, 135, 2459-2461
11. Belmessieri, D.; Cordes, D. B.; Slawin, A. M. Z.; Smith, A. D. Org. Lett. 2013, 15, 3472-3475
12. Nicolaou, K. C.; Chen, J. S. Chem. Soc. Rev. 2009, 38, 2993-3009
13. Grondal, C.; Jeanty, M.; Enders, D. Nat. Chem. 2010, 2, 167-178
14. Noble, A.; Anderson, J. C. Chem. Rev. 2013, 113, 2887-2939
15. Jakubec, P.; Helliwell, M.; Dixon, D. J. Org. Lett. 2008, 10, 4267-4270
16. Pelletier, S. M.-C.; Ray, P. C.; Dixon, D. J. Org. Lett. 2009, 11, 4512-4515
17. Pelletier, S. M.-C.; Ray, P. C.; Dixon, D. J. Org. Lett. 2011, 13, 6406-6409
18. Anderson, J. C.; Stepney, G. J.; Mills, M. R.; Horsfall, L. R.; Blake, A. J.; Lewis, W. J. Org. Chem. 2011, 76, 1961-1971
19. Jakubec, P.; Cockfield, D. M.; Helliwell, M.; Raftery, J.; Dixon, D. J. Beilstein J. Org. Chem. 2012, 8, 567-578
20. Anderson, J. C.; Horsfall, L. R.; Kalogirou, A. S.; Mills, M. R.; Stepney, G. J.; Tizzard, G. J. J. Org. Chem. 2012, 77, 6186-6198
21. Aillaud, I.; Collin, J.; Hannedouche, J.; Schulz, E. Dalton Trans. 2007, 5105-5118
22. Hartwig, J. F. Nature 2008, 455, 314-322
23. Zeng, X. Chem. Rev. 2013, 113, 6864-6900
24. Wang, H.-F; Yang, T.; Xu, P.-F.; Dixon, D. J. Chem. Commun. 2009, 3916-3918
25. Patil, N. T.; Mutyala, A. K.; Lakshmi, P. G. V. V; Gajula, B.; Sridhar, B.; Pottireddygari, G. R.; Rao, T. P. J. Org. Chem. 2010, 75, 5963-5975
26. Gregory, A. W.; Jakubec, P.; Turner, P.; Dixon, D. J. Org. Lett. 2013, 15, 4330-4333
27. Barber, D. M.; Sanganee, H.; Dixon, D. J. Chem. Commun. 2011, 47, 4379-4381
28. Barber, D. M.; Sanganee, H. J.; Dixon, D. J. Org. Lett. 2012, 14, 5290-5293
29. Ďuriš, A.; Barber, D. M.; Sanganee, H. J.; Dixon, D. J. Chem. Commun. 2013, 49, 2777-2779
30. Doyle, A. G.; Jacobsen, E. N. Chem. Rev. 2007, 107, 5713-5743
31. Dondoni, A.; Massi, A. Angew. Chem., Int. Ed. 2008, 47, 4638-4660
32. Melchiorre, P.; Marigo, M.; Carlone, A.; Bartoli, G. Angew. Chem., Int. Ed. 2008, 47, 6138-6171
33. Giacalone, F.; Gruttadauria, M.; Agrigento, P.; Noto, R. Chem. Soc. Rev. 2012, 41, 2406-2447
34. Nugent, B. M.; Yoder, R. A.; Johnston, J. N. J. Am. Chem. Soc. 2004, 126, 3418-3419
35. Wang, C.-J.; Dong, X.-Q.; Zhang, Z.-H.; Xue, Z.-Y.; Teng, H.-L. J. Am. Chem. Soc. 2008, 130, 8606-8607
36. Rueping, M.; Antonchick, A. P. Org. Lett. 2008, 10, 1731-1734
37. Núñez, M. G.; Farley, A. J. M.; Dixon, D. J. J. Am. Chem. Soc. 2013, 135, 16348-16351
38. Shapiro, N.; Toste, F. D. Synlett 2010, 675-691
39. Corma, A.; Leyva-Pérez, A.; Sabater, M. J. Chem. Rev. 2011, 111, 1657-1712
40. Krause, N.; Winter, C. Chem. Rev. 2011, 111, 1994-2009
41. Rudolph, M.; Hashmi, A. S. K. Chem. Soc. Rev. 2012, 41, 2448-2462
42. Patil, N. T.; Lutete, L. M.; Nishina, N.; Yamamoto, Y. Tetrahedron Lett. 2006, 47, 4749-4751
43. LaLonde, R. L.; Sherry, B. D.; Kang, E. J.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 2452-2453
44. Kinder, R. E.; Zhang, Z.; Widenhoefer, R. A. Org. Lett. 2008, 10, 3157-3159
45. Butler, K. L.; Tragni, M.; Widenhoefer, R. A. Angew. Chem., Int. Ed. 2012, 51, 5175-5178
46. Higginbotham, M. C. M.; Bebbington, M. W. P. Chem. Commun. 2012, 48, 7565-7567
47. Pflästerer, D.; Dolbundalchok, P.; Rafique, S.; Rudolph, M.; Rominger, F.; Hashmi, A. S. K. Adv. Synth. Catal. 2013, 355, 1383-1393
48. McCooey, S. H.; Connon, S. J. Angew. Chem., Int. Ed. 2005, 44, 6367-6370
49. Vakulya, B.; Varga, S.; Csámpai, A.; Soós, T. Org. Lett. 2005, 7, 1967-1969
50. Ye, J.; Dixon, D. J.; Hynes, P. S. Chem. Commun. 2005, 4481-4483
51. Li, B.; Jiang, L.; Liu, M.; Chen, Y.; Ding, L.; Wu, Y. Synlett 2005, 603-606
52. Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003, 125, 12672-12673
53. Okino, T.; Nakamura, S.; Furukawa, T.; Takemoto, Y. Org. Lett. 2004, 6, 625-627
54. Xu, X.; Furukawa, T.; Okino, T.; Miyabe, H.; Takemoto, Y. Chem.-Eur. J. 2006, 12, 466-476
55. Control experiments conducted using 10 mol % of both gold and silver salts resulted in lower isolated yields of pyrrolidine 4a. Similar observations on the "silver effect" in gold catalysis have been previously reported; see: Wang, D.; Cai, R.; Sharma, S.; Jirak, J.; Thummanapelli, S. K.; Akhmedov, N. G.; Zhang, H.; Liu, X.; Petersen, J. L.; Shi, X. J. Am. Chem. Soc. 2012, 134, 9012
56. Hashmi, A. S. K.; Häffner, T.; Yang, W.; Pankajakshan, S.; Schäfer, S.; Schultes, L.; Rominger, F.; Frey, W. Chem.-Eur. J. 2012, 18, 10480-10486
57. Zhou, J. Chem.-Asian J. 2010, 5, 422-434
58. Hashmi, A. S. K.; Hubbert, C. Angew. Chem., Int. Ed. 2010, 49, 1010-1012
59. Patil, N. T.; Shinde, V. S.; Gajula, B. Org. Biomol. Chem. 2012, 10, 211-224
60. Loh, C. C. J.; Enders, D. Chem.-Eur. J. 2012, 18, 10212-10225
61. Du, Z.; Shao, Z. Chem. Soc. Rev. 2013, 42, 1337-1378
62. Belot, S.; Vogt, K. A.; Besnard, C.; Krause, N.; Alexakis, A. Angew. Chem., Int. Ed. 2009, 48, 8923-8926
63. Jensen, K. L.; Franke, P. T.; Arróniz, C.; Kobbelgaard, S.; Jørgensen, K. A. Chem.-Eur. J. 2010, 16, 1750-1753
64. Monge, D.; Jensen, K. L.; Franke, P. T.; Lykke, L.; Jørgensen, K. A. Chem.-Eur. J. 2010, 16, 9478-9484
65. Loh, C. C. J.; Badorrek, J.; Raabe, G.; Enders, D. Chem.-Eur. J. 2011, 17, 13409-13414
66. Karplus, M. J. Am. Chem. Soc. 1963, 85, 2870-2871
67. Minch, M. J. Concepts Magn. Reson. 1994, 6, 41-56
68. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Burla, M. C.; Polidori, G.; Camalli, M. J. Appl. Crystallogr. 1994, 27, 435-436
69. Betteridge, P. W.; Carruthers, J. R.; Cooper, R. I.; Prout, K.; Watkin, D. J. J. Appl. Crystallogr. 2003, 36, 1487
70. Cooper, R. I.; Thompson, A. L.; Watkin, D. J. J. Appl. Crystallogr. 2010, 43, 1100-1107
71. Flack, H. D. Acta Crystallogr. 1983, A39, 876-881
72. Flack, H. D.; Bernardinelli, G. J. Appl. Crystallogr. 2000, 33, 1143-1148
73. Thompson, A. L.; Watkin, D. J. Tetrahedron: Asymmetry 2009, 20, 712-717
74. Thompson, A. L.; Watkin, D. J. J. Appl. Crystallogr. 2011, 44, 1017-1022