Efficient synthesis of cis-3-substituted prolines by bidentate-assisted palladium catalysis

European Journal of Organic Chemistry

Volumn 2015, Issue 1, 2015, Pages 142-151

  Feng, Ruokun ^a   Wang, Binjie ^a   Liu, Yue ^a   Liu, Zhanxiang ^a   Zhang, Yuhong ^a,b  

^a ZHEJIANG UNIVERSITY   (China)

^b LANZHOU UNIVERSITY   (China)

Author keywords

Amino acids; C H activation; Directing groups; Homogeneous catalysis; Palladium; Proline

Indexed keywords

EID: 84919681734     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201403191     Document Type: Article

References (73)

1. a) K. J. Jensen (Ed.), Peptide and Protein Design for Biopharmaceutical Applications, Wiley & Sons, Chichester, UK, 2009;
2. b) N. G. Delaney, V. Madison, J. Am. Chem. Soc. 1982, 104, 6636;
3. c). M. W. MacArthur, J. M. Thornton, J. Mol. Biol. 1991, 218, 397;
4. d). G. D. Rose, L. M. Gierasch, J. A. Smith, Adv. Protein Chem. 1985, 37, 1.
5. a) C. Mothes, C. Caumes, A. Guez, H. Boullet, T. Gendrineau, S. Darses, N. Delsuc, R. Moumné, B. Oswald, O. Lequin, P. Karoyan, Molecules 2013, 18, 2307;
6. b) P. Fatas, A. I. Jimenez, I. M. Calaza, C. Cativiela, Org. Biomol. Chem. 2012, 10, 640.
7. For reviews on organocatalysis, see: a) P. I. Dalko, L. Moisan, Angew. Chem. Int. Ed. 2004, 43, 5138;
8. Angew. Chem. 2004, 116, 5248;
9. b) A. Berkessel, H. Groger (Eds.), Asymmetric Organocatalysis, Wiley-VCH, Weinheim, Germany, 2005;
10. c) Y. Hayashi, J. Synth. Org. Chem. Jpn. 2005, 63, 464;
11. d) B. List, Chem. Commun. 2006, 819;
12. e) M. Marigo, K. A. Jørgensen, Chem. Commun. 2006, 2001;
13. f) M. J. Gaunt, C. C. C. Johansson, A. McNally, N. T. Vo, Drug Discovery Today 2007, 12, 8;
14. g) P. I. Dalko (Ed.), Enantioselective Organocatalysis, Wiley-VCH, Weinheim, Germany, 2007;
15. h) A. Dondoni, A. Massi, Angew. Chem. Int. Ed. 2008, 47, 4638;
16. Angew. Chem. 2008, 120, 4716;
17. i) P. Melchiorre, M. Marigo, A. Carlone, G. Bartoli, Angew. Chem. Int. Ed. 2008, 47, 6138;
18. Angew. Chem. 2008, 120, 6232.
19. For selected papers on the synthesis of 3-substituted prolines, see: a) R. Sharma, W. D. Lubell, J. Org. Chem. 1996, 61, 202;
20. b) Y. N. Belokon, A. G. Bulychev, V. A. Pavlov, V. M. Belikov, J. Chem. Soc. Perkin Trans. 1 1988, 2075;
21. c) A. I. Mcyers, L. Snyder, J. Org. Chem. 1992, 57, 3814.
22. J. Y. L. Chung, J. T. Wasicak, W. A. Arnold, C. S. May, A. M. Nadzan, M. W. Holladay, J. Org. Chem. 1990, 55, 270.
23. For selected reviews on C-C-bond formation through C-H activation, see: a) D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174;
24. b) C.-L. Sun, B.-J. Li, Z.-J. Shi, Chem. Rev. 2010, 111, 1293;
25. c) L. Ackermann, Chem. Rev. 2011, 111, 1315;
26. d) R. Jana, T. P. Pathak, M. S. Sigman, Chem. Rev. 2011, 111, 1417;
27. e) J. Le Bras, J. Muzart, Chem. Rev. 2011, 111, 1170;
28. f) C. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215;
29. g) A. F. M. Noisier, M. A. Brimble, Chem. Rev. 2014, 114, 8775.
30. For selected papers on new directing groups for C-H activation, see: a) P. Gandeepan, C.-H. Cheng, J. Am. Chem. Soc. 2012, 134, 5738;
31. b) M. Yu, Y. Xie, C. Xie, Y. Zhang, Org. Lett. 2012, 14, 2164;
32. c) J. Yao, M. Yu, Y. Zhang, Adv. Synth. Catal. 2012, 354, 3205;
33. d) X.-S. Zhang, Q.-L. Zhu, Y.-F. Zhang, Y.-B. Li, Z.-J. Shi, Chem. Eur. J. 2013, 19, 11898;
34. e) B. Wang, C. Shen, J. Yao, H. Yin, Y. Zhang, Org. Lett. 2014, 16, 46;
35. f) Z. Liang, L. Ju, Y. Xie, L. Huang, Y. Zhang, Chem. Eur. J. 2012, 18, 15816;
36. g) Y. Lu, D.-H. Wang, K. M. Engle, J.-Q. Yu, J. Am. Chem. Soc. 2010, 132, 5916;
37. h) Y. Lu, D. Leow, X. Wang, K. M. Engle, J.-Q. Yu, Chem. Sci. 2011, 2, 967;
38. i) C. Huang, B. Chattopadhyay, V. Gevorgyan, J. Am. Chem. Soc. 2011, 133, 12406;
39. j) L. Y. Chan, S. Kim, T. Ryu, P. H. Lee, Chem. Commun. 2013, 49, 4682;
40. k) X. Meng, S. Kim, Org. Lett. 2013, 15, 1910;
41. l) T. Ryu, J. Kim, Y. Park, S. Kim, P. H. Lee, Org. Lett. 2013, 15, 3986;
42. m) W. Li, Z. Xu, P. Sun, X. Jiang, M. Fang, Org. Lett. 2011, 13, 1286;
43. n) N. Hoshiya, T. Kobayashi, M. Arisawa, S. Shuto, Org. Lett. 2013, 15, 6202;
44. o) R. Parella, B. Gopalakrishnan, S. A. Babu, Org. Lett. 2013, 15, 3238;
45. p) B. V. S. Reddy, G. Revathi, A. S. Reddy, J. S. Yadav, Synlett 2011, 2374.
46. V. G. Zaitsev, D. Shabashov, O. Daugulis, J. Am. Chem. Soc. 2005, 127, 13154.
47. L. D. Tran, O. Daugulis, Angew. Chem. Int. Ed. 2012, 51, 5188;
48. Angew. Chem. 2012, 124, 5278.
49. a) Y. Feng, G. Chen, Angew. Chem. Int. Ed. 2010, 49, 958;
50. Angew. Chem. 2010, 122, 970;
51. b) G. He, G. Chen, Angew. Chem. Int. Ed. 2011, 50, 5192;
52. Angew. Chem. 2011, 123, 5298;
53. c) S.-Y. Zhang, G. He, Y. Zhao, K. Wright, W. A. Nack, G. Chen, J. Am. Chem. Soc. 2012, 134, 7313;
54. d) S.-Y. Zhang, Q. Li, G. He, W. A. Nack, G. Chen, J. Am. Chem. Soc. 2013, 135, 12135.
55. a) K. Chen, F. Hu, S.-Q. Zhang, B.-F. Shi, Chem. Sci. 2013, 4, 3906;
56. b) Q. Zhang, K. Chen, W. Rao, Y. Zhang, F.-J. Chen, B.-F. Shi, Angew. Chem. Int. Ed. 2013, 52, 13588;
57. Angew. Chem. 2013, 125, 13833.
58. N. Rodríguez, J. A. Romero-Revilla, M. Á. Fernández-Ibáñez, J. C. Carretero, Chem. Sci. 2013, 4, 175.
59. a) R. Giri, N. Maugel, J.-J. Li, D.-H. Wang, S. P. Breazzano, L. B. Saunders, J.-Q. Yu, J. Am. Chem. Soc. 2007, 129, 3510;
60. b) D.-H. Wang, T.-S. Mei, J.-Q. Yu, J. Am. Chem. Soc. 2008, 130, 17676;
61. c) M. Wasa, K. M. Engle, J.-Q. Yu, J. Am. Chem. Soc. 2010, 132, 3680.
62. a) H. A. Chiong, Q.-N. Pham, O. Daugulis, J. Am. Chem. Soc. 2007, 129, 9879;
63. b) Y. Kametani, T. Satoh, M. Miura, M. Nomura, Tetrahedron Lett. 2000, 41, 2655.
64. CCDC-1023265 contains the supplementary crystallographic data for compound 3dm. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
65. a) W. Yu, H. Tang, X. Cong, B. Rao, C. Wu, X. Zeng, Org. Lett. 2014, 16, 2248;
66. b) M. Li, J. Dong, X. Huang, K. Li, Q. Wu, F. Song, J. You, Chem. Commun. 2014, 50, 3944;
67. c) Q. Zhang, X.-S. Yin, S. Zhao, S.-L. Fang, B.-F. Shi, Chem. Commun. 2014, 50, 8353.
68. Y. Masato, K. Taku, 2010123006, 2010.
69. During the submission of our manuscript, similar work was published by Bull's group: D. P. Affron, O. A. Davis, J. A. Bull, Org. Lett. 2014, 16, 4956.
70. A. Chatterjee, M. Sasikumar, N. N. Joshi, Synth. Commun. 2007, 37, 1727.
71. K. C. Harper, S. C. Vilardi, M. S. Sigman, J. Am. Chem. Soc. 2013, 135, 2482.
72. a) T. Thanh, K. Kristine, O. Daugulis, J. Am. Chem. Soc. 2013, 135, 9342;
73. b) O. William, A. C. Moss, R. W. Jones, F. M. Mary, C. M. Kieran, H. B. Robert, J. H. Neil, G. Timothy, J. Chem. Soc. Perkin Trans. 1 1992, 2615.