Highly enantioselective friedel-crafts reaction of thiophenes with glyoxylates: Formal synthesis of duloxetine

Organic Letters

Volumn 11, Issue 20, 2009, Pages 4636-4639

  Majer, Jakub ^a   Kwlatkowskl, Plotr ^a,b   Jurczak, Janusz ^a,b  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

^b UNIVERSITY OF WARSAW   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; DULOXETINE; GLYOXYLIC ACID DERIVATIVE; ORGANOMETALLIC COMPOUND; THIOPHENE DERIVATIVE;

ARTICLE; CHEMISTRY; ENZYME SPECIFICITY; STEREOISOMERISM; SYNTHESIS;

ACETATES; GLYOXYLATES; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM; SUBSTRATE SPECIFICITY; THIOPHENES;

EID: 70349898271     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901906r     Document Type: Article

References (38)

1. (a) Wu, C.; Decker, E. R.; Blok, N.; Bui, H.; You, T. J.; Wang, J.; Bourgoyne, A. R.; Knowles, V.; Berens, K. L.; Holland, G. W.; Brock, T. A.; Dixon, R. A. F. J. Med. Chem. 2004, 47, 1969.
2. (b) Oberdorf, C.; Schepmann, D.; Vela, J. M.; Diaz, J. L.; Holenz, J.; Wünsch, B. J. Med. Chem. 2008, 51, 6531.
3. (c) Romagnoli, R.; Baraldi, P. G.; Carrion, M. D.; Cara, C. L.; Cruz-Lopez, O.; Iaconinoto, M. A.; Preti, D.; Shryock, J. C.; Moorman, A. R.; Vincenzi, F.; Varani, K.; Borea, P. A. J. Med. Chem. 2008, 51, 5875.
4. (d) Wang, W. L.; Chai, S. C.; Huang, M.; He, H. Z.; Hurley, T. D.; Ye, Q. Z. J. Med. Chem. 2008, 51, 6110.
5. (a) Hwang, I. T.; Kim, H. R.; Jeon, D. J.; Hong, K. S.; Song, J. H.; Cho, K. Y. J. Agric. Food Chem. 2005, 53, 8639.
6. (b) Fokialakis, N.; Cantrell, C. L.; Duke, S. O.; Skaltsounis, A. L.; Wedge, D. E. J. Agric. Food Chem. 2006, 54, 1651.
7. Lamberth, C.; Jeanguenat, A.; Cederbaum, F.; Mesmaeker, A.; Zeller, M.; Kempf, H. J.; Zeun, R. Bioorg. Med. Chem. 2008, 16, 1531.
8. (a) Yu, J.; Holdcroft, S. Chem. Mater. 2002, 14, 3705.
9. (b) Narasimhaswamy, T.; Somanathan, N.; Lee, D. K.; Ramamoorthy, A. Chem. Mater. 2005, 17, 2013.
10. (c) Querner, C.; Benedetto, A.; Demadrille, A.; Rannou, P.; Reiss, P. Chem. Mater. 2006, 18, 4817.
11. (a) Gao, J.; Martell, A. E. Org. Biomol. Chem. 2003, 1, 2801.
12. (b) Gao, M. Z.; Kong, D.; Clearfield, A.; Zingaro, R. A. Tetrahedron Lett. 2004, 45, 5649.
13. (c) Bandini, M.; Benaglia, M.; Quinto, T.; Tommasi, S.; Umani-Ronchi, A. Adv. Synth. Catal. 2006, 348, 1521.
14. (d) Zhang, X. Q.; Li, Y. Y.; Zhang, H.; Gao, J. X. Tetrahedron: Asymmetry 2007, 18, 2049.
15. (a) Barbarella, G.; Melucci, M.; Sotgiu, G. Adv. Mater. 2005, 17, 1581.
16. (b) Melucci, M.; Barbarella, G.; Gazzano, M.; Cavallini, M.; Biscarini, F.; Bongini, A.; Piccinelli, F.; Monari, M.; Bandini, M.; Umani-Ronchi, A.; Biscarini, P. Chem.-Eur. J. 2006, 12, 7304.
17. Dore, K.; Dubus, S.; Ho, H.-A.; Levesque, I.; Brunette, M.; Corbeil, G.; Boissinot, M.; Boivin, G.; Bergeron, M. G.; Boudreau, D.; Leclerc, M. J. Am. Chem. Soc. 2004, 126, 4240.
18. For a recent review in asymmetric F-C reaction, see: Poulsen, T. B.; Jørgensen, K. A. Chem. Rev. 2008, 108, 2903.
19. Cyrañski, M. K.; Krygowski, T. M.; Katritzky, A. R.; Schleyer, P. v. R. J. Org. Chem. 2002, 67, 1333.
20. (a) Gathergood, N.; Zhuang, W.; Jørgensen, K. A. J. Am. Chem. Soc. 2000, 122, 12517.
21. (b) Yuan. Y.; Wang. X.; Li, X.; Ding, K. J. Org. Chem. 2004, 69, 146.
22. (a) Dong, H.-M.; Lu, H.-H.; Lu, L.-Q.; Chen, C.-B.; Xiao, W.-J. Adv. Synth. Catal. 2007, 349, 1597.
23. (b) Li, H.; Wang, Y.-Q.; Deng, L. Org. Lett. 2006, 8, 4063.
24. Majer, J.; Kwiatkowski, P.; Jurczak, J. Org. Lett. 2008, 10, 2955.
25. (a) Zhuang, W.; Gathergood, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2001, 66, 1009.
26. (a) Saaby, S.; Bayón, P.; Aburel, P. S.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 4352.
27. (b) Shirakawa, S.; Berger, R.; Leighton, J. L. J. Am. Chem. Soc. 2005, 127, 2858.
28. (a) Zhang, W.; Wang, P. G. J. Org. Chem. 2000, 65, 4732.
29. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940.
30. Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467.
31. Ishii, A.; Soloshonok, V. A.; Mikami, K. J. Org. Chem. 2000, 65, 1597.
32. Other alkyl glyoxylates were also investigated in this reaction; for tert-butyl and isopropyl glyoxylates, the yields and enantioselectivity were lower compared to n-butyl glyoxylate.
33. Wong, D. T.; Robertson, D. W.; Bymaster, F. P.; Krushinski, J. H.; Reid, L. R. Life Sei. 1988, 43, 2049.
34. Kornstein, S. G.; Russell. J. M.; Spann, M. E.; Grits-Christoph, P.; Ball, S. G. Expert Rev. Neurother. 2009, 9, 155.
35. (a) Ratovelomanana-Vidal, V.; C. Girard, C.; R. Touati, R.; J. P. Tranchier, J. P.; B. Ben, B.; Hassine, B. B.; J. P. Genêt, J. P. Adv. Synth. Catal. 2003, 345, 261.
36. (b) Kamal, A.; Khanna, G. B. R.; Ramu, R.; Krishnaji, T. Tetrahedron Lett. 2003, 44, 4783.
37. (c) Genov, D. G.; Ager, D. J. Angew. Chem., Int. Ed. 2004, 43, 2816.
38. (d) Kuo, F.; Gillespie, T. A.; Kulanthaivel, P.; Lantz, R. J.; Ma, T. W.; Nelson, D. L.; Threlkeld, P. G.; Wheeler, W. J.; Yi, P.; Zmijewski, M. Bioorg. Med. Chem. Lett. 2004, 14, 3481.