Montmorillonite K10 clay: An efficient catalyst for the one-pot stereoselective synthesis of β-acetamido ketones

Journal of Organic Chemistry

Volumn 68, Issue 14, 2003, Pages 5735-5738

  Bahulayan, D ^a   Das, Saibal Kumar ^b   Iqbal, Javed ^a,b  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

^b DR REDDY'S LABORATORIES LTD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; CLAY; SYNTHESIS (CHEMICAL);

MONTMORILLONITE;

KETONES;

BETA ACETAMIDO KETONE DERIVATIVE; KETONE DERIVATIVE; MONTMORILLONITE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CLAY; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037662023     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020734p     Document Type: Article

References (38)

1. (a) Clark, J. H. Catalysis of Organic Reactions by Supported Inorganic Reagents; VCH: New York, 1994.
2. (b) Cornélis, A.; Laszlo, P. Synlett 1994, 155.
3. (c) Clark, J. H.; Macquarrie, D. J. Chem. Commun. 1998, 853.
4. (d) Varma, R. S.; Naicker, K. P.; Aschberger, J. Synth. Commun. 1999, 29, 2823.
5. (e) Meshram, H. M.; Sumithra, G.; Reddy, G. S.; Ganesh, Y. S. S.; Yadav, J. S. Synth. Commun. 1999, 29, 2807.
6. (f) Bahulayan, D.; Sukumar, R.; Sabu, K. R.; Lalithambika, M. Green Chem. 1999, 1, 191.
7. (g) Choudary, B. M.; Sateesh, M.; Kantham, M. L.; Rao, K. K.; Ramprasad, K. V.; Raghavan, K. V.; Sharma, J. A. R. P. Chem. Commun. 2000, 25, 1.
8. (h) Samajdar, S.; Becker, F. R.; Naik, P. K. Tetrahedron Lett. 2000, 41, 8017.
9. (i) Bahulayan, D.; Narayan, G.; Sreekumar, V.; Lalithambika, M. Synth. Commun. 2002, 32, 3565.
10. Clark, J. H.; Macquarrie, D. J. Chem. Soc. Rev. 1996, 303.
11. (a) Roudier, J.-F.; Foucaud, A. Tetrahedron Lett. 1984, 25, 4375.
12. (b) Chunchatprasert, L.; Rao, K. R. N.; Shannon, P. V. R. J. Chem. Soc., Perkin. Trans. 1 1992, 1779.
13. (c) Sieskind, O.; Albrecht, P. Tetrahedron Lett. 1993, 34, 1197.
14. (d) Gautier, E. C. L.; Graham, A. E.; McKillop, A.; Standen, S. P.; Taylor, R. L. K. Tetrahedron Lett. 1997, 38, 1881.
15. (e) Venkatachalapathy, C.; Pitchumani, K. Tetrahedron 1997, 53, 2581.
16. (f) Kannan, P.; Sevvel, R.; Rajagopal, S.; Pitchumani, K.; Srinivasan, C. Tetrahedron 1997, 53, 7635.
17. (g) Li, T.-S.; Wang, J.-X.; Zheng, X.-J. J. Chem. Soc., Perkin. Trans. 1 1998, 3957.
18. (h) Bushmelev, V. A.; Genaev, A. M.; Shubin, V. G. Russ. J. Org. Chem. 1999, 35, 62.
19. (i) Ohmura, H.; Smyth, G. D.; Mikami, K. J. Org. Chem. 1999, 64, 6056.
20. (j) Poupaert, J. H.; Bukuru, J.; Gozzo, A. Monatsh. Chem. 1999, 130, 929.
21. (k) Shaikh, N. S.; Gajare, A. S.; Deshpande, V. H.; Bedekar, A. V. Tetrahedron Lett. 2000, 41, 385.
22. (l) Avalos, M.; Babiano, R.; Bravo, J. L.; Cintas, P.; Jimenez, J. L.; Palacios, J. C. Tetrahedron Lett. 1998, 39, 9301.
23. (a) Texier-Boullet, F.; Latouche, R.; Hamelin, J. Tetrahedron Lett. 1993, 34, 2123.
24. (b) Perez, E. R.; Marrero, A. L.; Perez, R.; Autie, M. A. Tetrahedron Lett. 1995, 36, 1779.
25. (c) Ben-Alloum, A.; Bakkas, S.; Soufiaoui, M. Tetrahedron Lett. 1997, 38, 6395.
26. (d) Bolourtchian, M.; Zadmard, R.; Saidi, M. R. Synth. Commun. 1998, 28, 2017.
27. (e) Mojtahedi, M. M.; Saidi, M. R.; Bolourtchian, M. J. Chem. Res. Synop. 1999, 128.
28. (f) Bougrin, K.; Loupy, A.; Petit, A.; Daou, B.; Soufiaoui, M. Tetrahedron 2001, 57, 163.
29. (a) For a review see: Domling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168.
30. (b) Terret, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135.
31. (c) Thomson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555.
32. (d) Ellman, J. A. Acc. Chem. Res. 1996, 29, 132.
33. (a) Bhatia, B.; Reddy, M. M.; Iqbal, J. J. Chem. Soc., Chem. Commun. 1994, 713.
34. (b) Reddy, M. M.; Bhatia, B.; Iqbal, J. Tetrahedron Lett. 1995, 36, 4877.
35. (c) Mukhopadhyay, M.; Bhatia, B.; Iqbal, J. Tetrahedron Lett. 1997, 38, 1083.
36. (d) Prbhakaran, E. N.; Iqbal, J. J. Org. Chem. 1999, 64, 3339.
37. (e) For related three-component coupling, see: Armstrong, R. W.; Combs, A. W.; Templest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123.
38. (f) Rao, I. N.; Prabhakaran, E. N.; Das, S. K.; Iqbal, J. J. Org. Chem. 2003, 68, 4079.