Enantioselective benzoylation of α-amino esters using (S)-1-benzoyl-2-(α-acetoxyethyl)benzimidazole, a chiral benzimidazolide

Journal of Organic Chemistry

Volumn 72, Issue 19, 2007, Pages 7435-7438

  Karnik, Anil V ^a   Kamath, Suchitra S ^a  

^a UNIVERSITY OF MUMBAI   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ESTERS; ARYL SUBSTITUENTS; ENANTIOSELECTIVE BENZOYLATION; REACTION CONDITIONS;

ACYLATION; BENZENE; CHIRALITY; ENANTIOSELECTIVITY; SUBSTITUTION REACTIONS;

ESTERS;

1 BENZOYL 2 (ALPHA ACETOXYETHYL)BENZIMIDAZOLE; ALPHA AMINO ESTER DERIVATIVE; BENZIMIDAZOLE DERIVATIVE; ESTER DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CHIRALITY; ENANTIOSELECTIVITY; REACTION ANALYSIS; SYNTHESIS;

ACYLATION; AMINO ACIDS; BENZIMIDAZOLES; ESTERS; STEREOISOMERISM;

EID: 34548742218     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070962p     Document Type: Article

References (37)

1. (a) Arp, F. O.; Fu, G. C. J. Am. Chem. Soc. 2006, 128, 14264.
2. (b) Suzuki, Y.; Yamauchi, K.; Muramatsu, K.; Sato, M. Chem. Commun. 2004, 2770.
3. (c) Al-Sehemi, A. G.; Atkinson, R. S.; Fawcett, J.; Russell, D. R. Tetrahedron Lett. 2000, 41, 2239.
4. (d) Kawabata, T.; Yamamoto, K.; Momose, Y.; Yoshida, H.; Nagaoka, Y.; Fuji, K. Chem. Commun. 2001, 2700.
5. (e) Fu, G. C. Acc. Chem. Res. 2004, 37, 542.
6. (f) Birman, V. B.; Li, X. Org. Lett. 2006, 8, 1351.
7. (g) Miller, S. J.; Copeland, G. T.; Papaioannou, N.; Horstmann, T. E.; Ruel, E. M. J. Am. Chem. Soc. 1998, 120, 1629.
8. (a) Cho, B.-K.; Park, H.-Y.; Seo, J.-H.; Kinnera, K.; Lee, B.-S.; Kim, B.-G. Biotechnol. Bioeng. 2004, 88, 512.
9. (b) Zhao, H.; Malhotra, S. V. Biotechnol. Lett. 2002, 24, 1257.
10. (c) Brown, S. A.; Parker, M.-C.; Turner, N. J. Tetrahedron: Asymmetry 2000, 11, 1687.
11. Al-Sehemi, A. G.; Atkinson, R. S.; Fawcett, J. J. Chem. Soc., Perkin Trans. 1 2002, 257.
12. Arseniyadis, S.; Valleix, A.; Wagner, A.; Mioskowski, C. Angew. Chem., Int. Ed. 2004, 43, 3314.
13. (a) Bommarius, A. S.; Schwann, M.; Drauz, K. J. Mol. Catal. B: Enzymatic 1998, 5, 1.
14. (b) Angle, S. R.; Henry, R. M. J. Org. Chem. 1997, 62, 8549.
15. (c) Paruszewski, R.; Strupinska, M.; Stables, J. P.; Swiader, M.; Czuczwar, S.; Kleinrok, Z.; Turski, W. Chem. Pharm. Bull. 2001, 49, 629
16. (d) Fedi, V.; Altamura, M.; Balacco, G.; Canfarini, F.; Criscuoli, M.; Giannotti, D.; Giolitti, A.; Giuliani, S.; Guidi, A.; Harmat, N. J. S.; Nannicini, R.; Pasqui, F.; Patacchini, R.; Perrotta, E.; Tramontana, M.; Triolo, A.; Maggi, C. A. J. Med. Chem. 2004, 47, 6935.
17. (e) Yurek-George, A.; Habens, F.; Brimmell, M.; Packham, G.; Ganesan, A. J. Am. Chem. Soc. 2004, 126, 1030.
18. (f) Humphrey, J. M.; Chamberlin, A. R. Chem. Rev. 1997, 97, 2243.
19. (a) Shiraiwa, T.; Ohta, A.; Miyazaki, H.; Gogun, Y.; Kurokawa, H. Chirality 1997, 9, 386.
20. (b) Krasnov, V. P.; Zhdanova, E. A.; Solieva, N. Z.; Sadretdinova, L. S.; Bukrina, I. M.; Demin, A. M.; Levit, G. L.; Ezhikova, M. A.; Kodess, M. I. Russ. Chem. Bull. Int. Ed. 2004, 53, 1331.
21. (c) Marin, J.; Didierjean, C.; Aubry, A.; Casimir, J.-R.; Briand, J.-P.; Guichard, G. J. Org. Chem. 2004, 69, 130.
22. (d) Krasnov, V. P.; Levit, G. L.; Korolyova, M. A.; Bukrina, I. M.; Sadretdinova, L. S.; Andreeva, I. N.; Charushin, V. N.; Chupakhin, O. N. Russ. Chem. Bull. Int. Ed. 2004, 53, 1253.
23. (e) Katritzky, A. R.; Jiang, R.; Suzuki, K. J. Org. Chem. 2005, 70, 4993.
24. (a) Katritzky, A. R.; Abdel-Fattah, A. A. A.; Gromova, A. V.; Witek, R.; Steel, P. J. J. Org. Chem. 2005, 70, 9211.
25. (b) Katritzky, A. R.; Wang, Z.; Wang, M.; Wilkerson, C. R.; Hall, C. D.; Akhmedov, N. G. J. Org. Chem. 2004, 69, 6617.
26. (c) Katritzky, A. R.; He, H.-Y.; Suzuki, K. J. Org. Chem. 2000, 65, 8210.
27. (d) Katritzky, A. R.; Mohapatra, P. P.; Fedoseyenko, D.; Duncton, M.; Steel, P. J. J. Org. Chem. 2007, 72, 4268.
28. Phillips, M. A. J. Chem. Soc. 1928, 2393.
29. (a) Katritzky, A. R.; Asian, D. C.; Leeming, P.; Steel, P. J. Tetrahedron: Asymmetry 1997, 8, 1491.
30. (b) Katritzky, A. R.; Aslan, D. C.; Oniciu, D. C. Tetrahedron: Asymmetry 1998, 9, 2245.
31. (a) Liang, J.; Ruble, J. C.; Fu, G. C. J. Org. Chem. 1998, 63, 3154.
32. (b) Jones, J. B.; Niemann, C.; Hein, G. E. Biochemistry 1965, 4, 1735.
33. (c) Fryzuk, M. D.; Bosnich, B. J. Am. Chem. Soc. 1977, 99, 6262.
34. (d) Dondoni, A.; Perrone, D.; Semola, T. Synthesis 1995, 181.
35. (a) Bellemin-Laponnaz, S.; Tweddell, J.; Ruble, J. C.; Breitling, F. M.; Fu, G. C. Chem. Commun. 2000, 1009.
36. (b) Suarez, A.; Downey, C. W.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 11244.
37. (c) Schaus, S. E.; Brandes, B. D.; Larrow, J. F.; Tokunaga, M.; Hansen, K. B.; Gould, A. E.; Furrow, M. E.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 1307.