Modified asymmetric strecker reaction of aldehyde with secondary amine: A protocol for the synthesis of S-clopidogrel (an antiplatelet agent)

Journal of Organic Chemistry

Volumn 77, Issue 16, 2012, Pages 7076-7080

  Sadhukhan, Arghya ^a   Saravanan, S ^a   Khan, Noor Ul H ^a   Kureshy, Rukhsana I ^a   Abdi, Sayed H R ^a   Bajaj, Hari C ^a  

^a CSIR CENTRAL SALT AND MARINE CHEMICALS RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AMINONITRILES; ANTIPLATELET AGENT; CATALYTIC SYSTEM; CHIRAL CATALYST; CHIRAL PRODUCT; CLOPIDOGREL; HIGH ENANTIOSELECTIVITY; SECONDARY AMINES; SODIUM FLUORIDE; STRECKER REACTIONS;

ALDEHYDES; SODIUM;

ORGANIC COMPOUNDS;

ALDEHYDE; AMINE; BENZALDEHYDE; CLOPIDOGREL; FLUORIDE SODIUM; HYDROQUININE; MORPHOLINE; NITRILE;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHIRALITY; DRUG STRUCTURE; ENANTIOSELECTIVITY; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIZATION; STRECKER SYNTHESIS;

ALDEHYDES; AMINES; CATALYSIS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PLATELET AGGREGATION INHIBITORS; QUINIDINE; SODIUM FLUORIDE; STEREOISOMERISM; TICLOPIDINE;

EID: 84865206646     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo300642z     Document Type: Article

References (51)

1. Nájera, C.; Sansano, J. M. Chem. Rev. 2007, 107, 4584-4671
2. Gröger, H. Chem. Rev. 2003, 103, 2795-2827
3. Wang, J.; Liu, X.; Feng, X. Chem. Rev. 2011, 111, 6947-6983
4. Zuend, S. J.; Coughlin, M. P.; Lalonde, M. P.; Jacobsen, E. N. Nature 2009, 461, 968-970
5. Doyle, A. G.; Jacobsen, E. N. Chem. Rev. 2007, 107, 5713-5743
6. Skucas, E.; Ngai, M.-Y.; Komanduri, V.; Krische, M. J. Acc. Chem. Res. 2007, 40, 1394-1401
7. Merino, P; Marqués-López, E.; Tejero, T.; Herrera, R. Tetrahedron 2009, 65, 1219-1234
8. Martens, J. Chem. Cat. Chem. 2010, 2, 379-381
9. Soloshonok, V. A.; Izawa, K., Eds. Asymmetric Synthesis and Application of R-Amino Acids; American Chemical Society: Washington, DC, 2009; Vol. 1009.
10. Bommarius, A. S.; Schwarm, M.; Drauz, K. Chimia 2001, 55, 50-59
11. Enders, D.; Shilvock, J. P. Chem. Soc. Rev. 2000, 29, 359-373
12. Opatz, T. Synthesis 2009, 1941-1959
13. Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157-160
14. Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901-4902
15. Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem. 2000, 112, 1336-1338
16. Angew. Chem., Int. Ed. 2000, 39, 1279.
17. Pan, S. C.; Zhou, J.; List, B. Angew. Chem. 2007, 119, 618
18. Angew. Chem., Int. Ed. 2007, 46, 612-614.
19. Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012-10014
20. Jiao, Z. G.; Feng, X. M.; Liu, B.; Chen, F. X.; Zhang, G. L.; Jiang, Y. Z. Eur. J. Org. Chem. 2003, 3818-3826
21. Huang, J. L.; Liu, X. H.; Wen, Y. H.; Qin, B.; Feng, X. M. J. Org. Chem. 2007, 72, 204-208
22. Huang, X.; Huang, J. L.; Wen, Y. H.; Feng, X. M. Adv. Synth. Catal. 2006, 348, 2579-2584
23. Huang, J.; Corey, E. J. Org. Lett. 2004, 6, 5027-5029
24. Ooi, T.; Uematsu, Y.; Maruoka, K. J. Am. Chem. Soc. 2006, 128, 2548-2549
25. Rueping, M.; Sugiono, E.; Azap, C. Angew. Chem. 2006, 118, 2679-2681
26. Angew. Chem., Int. Ed. 2006, 45, 2617-2619.
27. Rueping, M.; Sugiono, E.; Moreth, S. A. Adv. Synth. Catal. 2007, 349, 759-764
28. Wen, Y. H.; Xiong, Y.; Chang, L.; Huang, J. L.; Liu, X. H.; Feng, X. M. J. Org. Chem. 2007, 72, 7715-7719
29. Takamura, M.; Hamashima, Y.; Usuda, H.; Kanai, M.; Shibasaki, M. Angew. Chem. 2000, 112, 1716-1718
30. Nogami, H.; Matsunaga, S.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2001, 42, 279-283
31. Wang, J.; Hu, X. L.; Jiang, J.; Gou, S. H.; Huang, X.; Liu, X. H.; Feng, X. M. Angew. Chem. 2007, 119, 8620-8622
32. Josephsohn, N. S.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 11594-11599
33. Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766
34. Masumoto, S.; Usuda, H.; Suzuki, M.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 5634-5635
35. Kato, N.; Suzuki, M.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2004, 45, 3147-3151
36. Khan, N. H.; Saravanan, S.; Kureshy, R. I.; Abdi, S. H. R.; Bajaj, H. C. Tetrahedron: Asymmetry 2010, 21, 2076-2080
37. Khan, N. H.; Saravanan, S.; Kureshy, R. I.; Abdi, S. H. R.; Sadhukhan, A.; Bajaj, H. C. J. Organomet. Chem. 2010, 695, 1133-1137
38. Seayad, A. M.; Ramalingam, B.; Yoshinaga, K.; Nagata, T.; Chai, C. L. L. Org. Lett. 2010, 12, 264-267
39. Lundgren, S.; Wingstrand, E.; Penhoat, M.; Moberg, C. J. Am. Chem. Soc. 2005, 127, 11592-11593
40. Martínez, R.; Ramón, D. J.; Yus, M. Tetrahedron Lett. 2005, 46, 8471-8474
41. Galletti, P.; Pori, M.; Giacomini, D. Eur. J. Org. Chem. 2011, 3896-3903
42. Mojtahedi, M. M.; Abaee, M. S.; Alishiri, T. Tetrahedron Lett. 2009, 50, 2322-2325
43. Rajabi, F.; Ghiassian, S.; Saidi, M. R. Green Chem. 2010, 12, 1349-1352
44. Harwood, L. M.; Drew, M. G. B.; Hughes, D. J.; Vickers, R. J. J. Chem. Soc., Perkin Trans. 1 2001, 1581-1587
45. Reingruber, R.; Baumann, T.; Dahmen, S.; Bräse, S. Adv. Synth. Catal. 2009, 351, 1019-1024
46. Bousquet, A.; Calet, S.; Heymes, A. U.S. Patent 5,132,435, 1992.
47. Bousquet, A.; Musolino, A. U.S. Patent 6,573,381B1, 2003.
48. Pandey, B; Lohray, V. B.; Lohray, B. B. U.S. Patent 2002/0177712A1, 2002.
49. Wang, L.; Shen, J.; Tang, Y.; Chen, Y.; Wang, W.; Cai, Z.; Du, Z. Org. Process Res. Dev. 2007, 11, 487-489
50. vander Meijden, M. W.; Leeman, M.; Gelens, E.; Noorduin, W. L.; Meekes, H.; van Enckevort, W. J. P.; Kaptein, B.; Vlieg, E.; Kellogg, R. M. Org. Process Res. Dev. 2009, 13, 1195-1198
51. Blinka, T. A.; Helmer, B. J.; West, R. Adv. Organomet. Chem. 1984, 23, 193