Regio- and stereospecific synthesis of C-3 functionalized proline derivatives by palladium catalyzed directed C(sp3)-H Arylation

Organic Letters

Volumn 16, Issue 18, 2014, Pages 4956-4959

  Affron, Dominic P ^a   Davis, Owen A ^a   Bull, James A ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL PRODUCT; IODINATED HYDROCARBON; PALLADIUM; PROLINE; PYRROLIDINE DERIVATIVE;

ANALOGS AND DERIVATIVES; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BIOLOGICAL PRODUCTS; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; HYDROCARBONS, IODINATED; MOLECULAR STRUCTURE; PALLADIUM; PROLINE; PYRROLIDINES; STEREOISOMERISM;

EID: 84919599867     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol502511g     Document Type: Article

References (76)

1. (a) MacArthur, M. W.; Thornton, J. M. J. Mol. Biol. 1991, 218, 397.
2. (b) Williamson, M. P. Biochem. J. 1994, 297, 249.
3. (a) Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748.
4. (b) Felpin, F.-X.; Lebreton, J. Eur. J. Org. Chem. 2003, 3693.
5. (c) Liddell, J. R. Nat. Prod. Rep. 2002, 19, 773.
6. (d) O'Hagan, D. Nat. Prod. Rep. 2000, 17, 435.
7. Taylor, R. D.; MacCoss, M.; Lawson, A. D. G. J. Med. Chem. 2014, 57, 5845.
8. (a) Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. Rev. 2007, 107, 5471.
9. (b) Panday, S. K. Tetrahedron: Asymmetry 2011, 22, 1817.
10. (a) Vo, C. T.; Bode, J. W. J. Org. Chem. 2014, 79, 2809.
11. (b) Han, M.; Jia, J.; Wang, W. Tetrahedron Lett. 2014, 55, 784.
12. (c) Pandey, G.; Banerjee, P.; Gadre, S. R Chem. Rev. 2006, 106, 4484.
13. (d) Gotoh, H; Okamura, D.; Ishikawa, H; Hayashi, Y. Org. Lett. 2009, 11, 4056.
14. (e) Chung, J. Y. L.; Wasicak, J. T.; Arnold, W. A.; May, C. S.; Nadzan, A. M.; Holladay, M. W. J. Org. Chem. 1990, 55, 270.
15. Selected references: (a) Mitchell, E. A; Peschiulli, A.; Lefevre, N; Meerpoel, L.; Maes, B. U. W. Chem.-Eur. J. 2012, 18, 10092.
16. (b) Zuo, Z.; MacMillan, D. W. C. J. Am. Chem. Soc. 2014, 136, 5257.
17. (c) Zuo, Z.; Ahneman, D.; Chu, L.; Terrett, J. A; Doyle, A G; MacMillan, D. W. C. Science 2014, 345, 437.
18. (d) Haldar, S.; Mahato, S.; Jana, C. K. Asian J. Org. Chem. 2014, 3, 44.
19. (e) Ma, L.; Chen, W.; Seidel, D. J. Am. Chem. Soc. 2012, 134, 15305.
20. (f) Bi, H.-P.; Zhao, L.; Liang, Y.-M.; Li, C.-J. Angew. Chem., Int. Ed. 2009, 48, 792.
21. (g) Gribkov, D. V.; Pastine, S. J.; Schnurch, M.; Sames, D. J. Am. Chem. Soc. 2007, 129, 11750.
22. (h) McNally, A.; Prier, C. K.; MacMillan, D. W. C. Science 2011, 334, 1114.
23. (i) Yoshikai, N; Meczkowski, A.; Matsumoto, A.; Ilies, L.; Nakamura, E. J. Am. Chem. Soc. 2010, 132, 5568.
24. (a) Beak, P.; Kerrick, S. T.; Wu, S.; Chu, J. J. Am. Chem. Soc. 1994, 116, 3231.
25. (b) Dearden, M. J.; Firkin, C. R; Hermet, J.-P. R; O'Brien, P. J. Am. Chem. Soc. 2002, 124, 11870.
26. (c) Beng, T. K.; Woo, J. S.; Gawley, R E. J. Am. Chem. Soc. 2012, 134, 14764.
27. (d) Campos, K. R; Klapars, A.; Waldman, J. H; Dormer, P. G; Chen, C. J. Am. Chem. Soc. 2006, 128, 3538.
28. (a) Pastine, S. J.; Gribkov, D. V.; Sames, D. J. Am. Chem. Soc. 2006, 128, 14220.
29. (b) Prokopcova, H; Bergman, S. D.; Aelvoet, K.; Smout, V.; Herrebout, W.; Van Der Veken, B.; Meerpoel, L.; Maes, B. U. W. Chem.-Eur. J. 2010, 16, 13063.
30. (a) Chatani, N; Asaumi, T.; Ikeda, T.; Yorimitsu, S.; Ishii, Y.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 2000, 122, 12882.
31. (b) Chatani, N; Asaumi, T.; Yorimitsu, S.; Ikeda, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 2001, 123, 10935.
32. (c) Schinkel, M.; Wang, L.; Bielefeld, K.; Ackermann, L. Org. Lett. 2014, 16, 1876.
33. For recent examples: (a) Allwood, D. M.; Blakemore, D. C.; Brown, A. D.; Ley, S. V. J. Org. Chem. 2014, 79, 328.
34. (b) Molander, G A.; Traister, K. M.; O'Neill, B. T. J. Org. Chem. 2014, 79, 5771.
35. (a) Ritchie, T. J.; Macdonald, S. J. F.; Young, RJ.; Pickett, S. D. Drug Discovery Today 2011, 16, 164.
36. (b) Lovering, F.; Bikker, J.; Humblet, C. J. Med. Chem. 2009, 52, 6752.
37. (c) Lovering, F. Med. Chem. Commun. 2013, 4, 515.
38. (a) Hung, A. W.; Ramek, A; Wang, Y.; Kaya, T.; Wilson, J. A.; Clemons, P. A.; Young, D. W. Proc. Natl. Acad. Sci. U. SA. 2011, 108, 6799.
39. (b) Nadin, A; Hattotuwagama, C; Churcher, I. Angew. Chem., Int. Ed. 2012, 51, 1114.
40. (c) Doveston, R; Marsden, S.; Nelson, A. Drug Discovery Today 2014, 19, 813.
41. (a) Morgan, K. F.; Hollingsworth, I. A.; Bull, J. A Chem. Commun. 2014, 50, 5203.
42. (b) Davis, O. A; Hughes, M.; Bull, J. A J. Org. Chem. 2013, 78, 3470.
43. Fragments targeted to comply with a modified 'rule-of-3': MW <300, cLogP <3; HBD ≤3; HBA ≤6. See: (a) Congreve, M.; Carr, R; Murray, C.; Jhoti, H. Drug Discovery Today 2003, 8, 876.
44. (b) Koster, H; Craan, T.; Brass, S.; Herhaus, C.; Zentgraf, M.; Neumann, L.; Heine, A.; Klebe, G J. Med. Chem. 2011, 54, 7784.
45. (c) Murray, C. W.; Rees, D. C. Nat. Chem. 2009, 1, 187.
46. (a) Mok, N. Y.; Brenk, R; Brown, N. J. Chem. Inf. Model. 2014, 54, 79.
47. (b) Over, B.; Wetzel, S.; Grutter, C.; Nakai, Y.; Renner, S.; Rauh, D.; Waldmann, H. Nat. Chem. 2013, 5, 21.
48. (a) Rouquet, G; Chatani, N. Angew. Chem., Int. Ed. 2013, 52, 11726.
49. (b) Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960.
50. (c) Baudoin, O. Chem. Soc. Rev. 2011, 40, 4902.
51. (d) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147.
52. (e) Chen, X.; Engle, K. M.; Wang, D.-H; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094.
53. (a) Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154.
54. (b) Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2010, 132, 3965.
55. (c) Nadres, E. T.; Santos, G. I. F.; Shabashov, D.; Daugulis, O. J. Org. Chem. 2013, 78, 9689.
56. For recent examples of complementary ligand enabled Pd0/PdII C-H arylation, see: (a) He, J.; Li, S.; Deng, Y.; Fu, H.; Laforteza, B. N.; Spangler, J. E.; Homs, A.; Yu, J.-Q. Science 2014, 343, 1216.
57. (b) Li, S.; Chen, G.; Feng, C.-G.; Gong, W.; Yu, J. J. Am. Chem. Soc. 2014, 136, 5267.
58. (c) Chan, K. S. L.; Wasa, M.; Chu, L.; Laforteza, B. N.; Miura, M.; Yu, J.-Q. Nat. Chem. 2014, 6, 146.
59. (d) Xiao, K.-J.; Lin, D. W.; Miura, M.; Zhu, R.-Y.; Gong, W.; Wasa, M.; Yu, J.-Q. J. Am. Chem. Soc. 2014, 136, 8138.
60. (a) Roman, D. S.; Charette, A. B. Org. Lett. 2013, 15, 4394.
61. (b) Parella, R.; Gopalakrishnan, B.; Babu, S. A. Org. Lett. 2013, 15, 3238.
62. (a) Gutekunst, W. R.; Baran, P. S. J. Am. Chem. Soc. 2011, 133, 19076.
63. (b) Gutekunst, W. R.; Gianatassio, R.; Baran, P. S. Angew. Chem., Int. Ed. 2012, 51, 7507.
64. (c) Parella, R.; Gopalakrishnan, B.; Babu, S. A. J. Org. Chem. 2013, 78, 11911.
65. (a) Rodríguez, N.; Romero-Revilla, J. A.; Fernández-Ibáñez, M. Á.; Carretero, J. C. Chem. Sci. 2013, 4, 175.
66. (b) Chen, K.; Hu, F.; Zhang, S.-Q.; Shi, B.-F. Chem. Sci. 2013, 4, 3906.
67. (c) Fan, M.; Ma, D. Angew. Chem., Int. Ed. 2013, 52, 12152.
68. Also see: (a) He, G.; Zhang, S.-Y.; Nack, W. A.; Li, Q.; Chen, G. Angew. Chem., Int. Ed. 2013, 52, 11124.
69. (b) He, G.; Chen, G. Angew. Chem., Int. Ed. 2011, 50, 5192.
70. (c) Zhang, S.-Y.; Li, Q.; He, G.; Nack, W. A.; Chen, G. J. Am. Chem. Soc. 2013, 135, 12135.
71. (d) Zhang, S.-Y.; He, G.; Nack, W. A.; Zhao, Y.; Li, Q.; Chen, G. J. Am. Chem. Soc. 2013, 135, 2124.
72. For Ni catalysis, see: (e) Aihara, Y.; Chatani, N. J. Am. Chem. Soc. 2014, 136, 898.
73. (f) Wu, X.; Zhao, Y.; Ge, H. J. Am. Chem. Soc. 2014, 136, 1789.
74. (a) Wu reported C-H amination at C-3 of a proline derivative: Sun, W.-W.; Cao, P.; Mei, R.-Q.; Li, Y.; Ma, Y.-L.; Wu, B. Org. Lett. 2014, 16, 480.
75. (c) For alkynylation on a tetrahydropyran derivative, see: He, J.; Wasa, M.; Chan, K. S. L.; Yu, J. J. Am. Chem. Soc. 2013, 135, 3387.
76. (d) For arylation of a tetrahydropyran derivative: Wasa, M.; Chan, K. S. L.; Zhang, X.; He, J.; Miura, M.; Yu, J. J. Am. Chem. Soc. 2012, 134, 18570.