Highly enantioselective synthesis of warfarin and its analogs by means of cooperative LiClO4/DPEN-catalyzed Michael reaction: Enantioselectivity enhancement and mechanism

Tetrahedron

Volumn 66, Issue 51, 2010, Pages 9708-9713

  Yang, Hua Meng ^a   Li, Li ^a   Jiang, Ke Zhi ^a   Jiang, Jian Xiong ^a   Lai, Guo Qiao ^a   Xu, Li Wen ^a,b  

^a HANGZHOU NORMAL UNIVERSITY   (China)

^b LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

DXJNKRISRBPCPO RCAPONPDSA N

Indexed keywords

1,2 DIPHENYLETHYLENEDIAMINE; 4 HYDROCOUMARIN; DIAMINE DERIVATIVE; LEWIS ACID; LITHIUM PERCHLORATE; UNCLASSIFIED DRUG; WARFARIN;

ARTICLE; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; MICHAEL ADDITION; PRIORITY JOURNAL;

EID: 78650200489     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.10.032     Document Type: Article

References (51)

1. Selected recent reviews, see:
2. C.F. Nising, and S. Bräse Chem. Soc. Rev. 37 2008 1218 1228
3. J. Christoffers, G. Koripelly, A. Rosiak, and M. Rossle Synthesis 2007 1279 1300
4. D. Enders, A. Saint-Dizier, M.I. Lannou, and A. Lenzen Eur. J. Org. Chem. 2006 29 49
5. L.W. Xu, and C.G. Xia Eur. J. Org. Chem. 2005 633 639
6. N. Halland, T. Hansen, and K.A. Jørgensen Angew. Chem., Int. Ed. 42 2003 4955 4957
7. N. Halland, T. Velgaard, and K.A. Jørgensen J. Org. Chem. 68 2003 5067 5074
8. H. Kim, C. Yen, P. Preston, and J. Chin Org. Lett. 8 2006 5239 5242
9. J.W. Xie, L. Yue, W. Chen, W. Du, J. Zhu, J.G. Deng, and Y.C. Chen Org. Lett. 9 2007 413 415
10. T.E. Kristensen, K. Vestli, F. Hansen, and T. Hansen Eur. J. Org. Chem. 2009 5185 5191
11. Z. Dong, L. Wang, X. Chen, X. Liu, L. Lin, and X. Feng Eur. J. Org. Chem. 2009 5192 5197
12. R.A.N. O'Reilly Engl. J. Med. 295 1976 354 357
13. H.P. Rang, M.M. Dale, J.M. Ritter, and P. Gardner Pharmacology 4th ed. 2001 Churchill Livingstone Philadelphia
14. Bardsley, H.J., Daly, A.K. PCT patent WO00/43003, 2000.
15. V. Farina, J.T. Reeves, C.H. Senanayake, and J.J. Song Chem. Rev. 106 2006 2734 2793
16. D. Fishelovitch, C. Hazan, S. Shaik, H.J. Wolfson, and R. Nussinov J. Am. Chem. Soc. 129 2007 1602 1611
17. B.D. West, S. Preis, C.H. Schroeder, and K.P. Link J. Am. Chem. Soc. 83 1961 2676 2679
18. A.S. Demir, C. Tanyeli, V. Gülbeyaz, and H. Akgün Turk. J. Chem. 20 1996 139 145
19. A. Robinson, H.Y. Li, and J. Feaster Tetrahedron Lett. 37 1996 8321 8324
20. Y. Tsuchiya, Y. Hamashima, and M. Sodeoka Org. Lett. 8 2006 4851 4854
21. G. Cravotto, G.M. Nano, G. Palmisano, and S. Tagliapietra Tetrahedron: Asymmetry 12 2001 707 709
22. See recent reviews:
23. A. Erkkila, I. Majander, and P.M. Pihko Chem. Rev. 107 2007 5416 5470
24. S. Mukherjee, J.W. Yang, S. Hoffmann, and B. List Chem. Rev. 107 2007 5471 5569
25. L.W. Xu, and Y. Lu Org. Biomol. Chem. 6 2008 2047 2053
26. L.W. Xu, J. Luo, and Y. Lu Chem. Commun. 2009 1807 1821
27. S. Bertelsen, and K.A. Jørgensen Chem. Soc. Rev. 38 2009 2178 2189
28. L.W. Xu, L. Li, and Z.H. Shi Adv. Synth. Catal. 352 2010 243 279 and references cited in
29. Y.D. Ju, L.W. Xu, L. Li, G.Q. Lai, H.Y. Qiu, J.X. Jiang, and Y.X. Lu Tetrahedron Lett. 49 2008 6773 6777
30. Z.Y. Jiang, H.M. Yang, Y.D. Ju, L. Li, M.X. Luo, G.Q. Lai, J.X. Jiang, and L.W. Xu Molecules 15 2010 2551 2563
31. J. Christoffers Synlett 2001 723 732
32. H.M. Yang, Y.H. Gao, L. Li, Z.Y. Jiang, G.Q. Lai, C.G. Xia, and L.W. Xu Tetrahedron Lett. 51 2010 3836 3839
33. Standard conditions: the enantioselective Michael reactions of 4-hydrocoumarin (1 mmol) to benzylideneacetone (1.2 mmol) were performed with 5 mol % of metal salt, 5 mol % of organocatalyst, 10 equiv of AcOH in THF (2 mL) and at room temperature for 24 h.
34. L. Yang, L.W. Xu, and C.G. Xia Tetrahedron Lett. 48 2007 1599 1603
35. Z. Shao, and H. Zhang Chem. Soc. Rev. 38 2009 2745 2755
36. C. Zhong, and X. Shi Eur. J. Org. Chem. 2010 2999 3025
37. Y.F. Cai, H.M. Yang, L. Li, K.Z. Jiang, G.Q. Lai, J.X. Jiang, and L.W. Xu Eur. J. Org. Chem. 2010 4986 4990
38. For recent examples, see:
39. L.S. Santos, Reactive Intermediates 2010 Wiley-VCH Weinheim
40. A.A. Sabino, A.H.L. Machado, C.R.D. Correia, and M.N. Eberlin Angew. Chem., Int. Ed. 43 2004 2514 2518
41. E.S. Orth, T.A.S. Brandão, H.M.S. Milagre, M.N. Eberlin, and F. Nome J. Am. Chem. Soc. 130 2008 2436 2437
42. C.A. Müller, and A. Pfaltz Angew. Chem., Int. Ed. 47 2008 3363 3366
43. C.A. Müller, C. Markert, A.M. Teichert, and A. Pfaltz Chem. Commun. 2009 1607 1618
44. V.M. Williams, J.R. Kong, B.J. Ko, Y. Mantri, J.S. Brodbelt, M.H. Baik, and M.J. Krische J. Am. Chem. Soc. 131 2009 16054 16062
45. C. Puchot, O. Samuel, E. Duñach, S. Zhao, C. Agami, and H.B. Kagan J. Am. Chem. Soc. 108 1986 2353 2357
46. D. Guillaneux, S.H. Zhao, O. Samuel, D. Rainford, and H.B. Kagan J. Am. Chem. Soc. 116 1994 9430 9439
47. C. Girard, and H.B. Kagan Angew. Chem., Int. Ed. 37 1998 2922 2959
48. M. Avalos, R. Babiano, P. Cintas, J.L. Jiménez, and J.C. Palacios Tetrahedron: Asymmetry 8 1997 2997 3017
49. D.G. Blackmond Acc. Chem. Res. 33 2000 402 411
50. F. Buono, P.J. Walsh, and D.G. Blackmond J. Am. Chem. Soc. 124 2002 13652 13653
51. M. Klussmann, H. Iwamura, S.P. Mathew, D.H. Wells Jr., U. Pandya, A. Armstrong, and D.G. Blackmond Nature 441 2006 621 623