β-cyclodextrin-mediated acetic acid catalyzed diastereoselective Mannich reaction in water

Synlett

Volumn 23, Issue 16, 2012, Pages 2328-2332

  Sukumari, Subbiah ^a   Azath, Ismail Abulkalam ^a   Pitchumani, Kasi ^a  

^a MADURAI KAMARAJ UNIVERSITY   (India)

Author keywords

Aqueous medium; Cyclodextrins; Diastereoselectivity; Mannich bases; Supramolecular chemistry

Indexed keywords

2 METHYL 1,3 DIPHENYL 3 (PHENYLAMINO)PROPAN 1 ONE; 3 [(4 CHLOROPHENYL)AMINO] 2 METHYL 1,3 DIPHENYLPROPAN 1 ONE; ACETIC ACID; BENZALDEHYDE; BETA CYCLODEXTRIN; CYCLODEXTRIN; CYCLOHEXANONE; UNCLASSIFIED DRUG; WATER;

ALDOL REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION; CRYSTAL STRUCTURE; ENANTIOMER; HYDROGEN BOND; MANNICH REACTION; PH; REACTION OPTIMIZATION; TEMPERATURE;

EID: 84865828048     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/S-0032-1317156     Document Type: Article

References (48)

1. (a) Kobayashi, S.; Mori, Y.; Fossey, J. S.; Salter, M. M. Chem. Rev. 2011, 111, 2626.
2. (b) Ma, J. A. Angew. Chem. Int. Ed. 2003, 42, 4290.
3. (c) Liu, M.; Sibi, M. P. Tetrahedron 2002, 58, 7991.
4. (d) Duthaler, R. O. Tetrahedron 1994, 50, 1539.
5. (a) Hayashi, Y.; Tsuboi, W.; Ashimine, I.; Urushima, T.; Shoji, M.; Sakai, K. Angew. Chem. Int. Ed. 2003, 42, 3677.
6. (b) Denmark, S.; Nicaise, O. J.-C. In Comprehensive Asymmetric Catalysis; Vol. 2; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999, 93.
7. (c) Arend, M.; Westermanm, B.; Risch. N. Angew. Chem. Int. Ed. 1998, 37, 1044.
8. For a recent review in this area, see: (a) Verkade, J. M. M.; Hemert, L. J. C. V.; Quaedflieg, P. J. L. M.; Rutjes, F. P. J. T. Chem. Soc. Rev. 2008, 37, 29.
9. (b) Ting, A.; Schaus, S. E. Eur. J. Org. Chem. 2007, 5797.
10. (c) For a short survey of highlights in this field, see: Marques, M. M. B. Angew. Chem. Int. Ed. 2006, 45, 348.
11. (a) List, B. J. Am. Chem. Soc. 2000, 122, 9336.
12. (b) Lou, S.; Taoka, B. M.; Ting, A.; Sehaus, S. E. J. Am. Chem. Soc. 2005, 127, 11256.
13. (c) Guo, Q.-X.; Liu, H.; Guo, C.; Leo, S.-W.; Gu, Y.; Ghong, L. Z. J. Am. Chem. Soc. 2007, 129, 3790.
14. Kobayashi, S.; Nagayama, S.; Busujima, T. Tetrahedron Lett. 1996, 37, 9221.
15. Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1998, 120, 2985.
16. Kobayashi, S.; Nagayama, S. J. Org. Chem. 1997, 62, 232.
17. Manabe, K.; Kobayashi, S. Org. Lett. 1999, 1, 1965.
18. Manabe, K.; Mori, Y.; Kobayashi, S. Tetrahedron 2001, 57, 2537.
19. Loh, T. P.; Liung, S. B. K. W.; Tan, K. L.; Wei, L. L. Tetrahedron 2000, 56, 3227.
20. Akiyama, T.; Takaya, J.; Kagoshima, H. Adv. Synth. Catal. 2002, 344, 338.
21. Boglio, C.; Lemiere, G.; Hasenknopf, B.; Thorimbert, S.; Lacote, E.; Malacria, M. Angew. Chem. Int. Ed. 2006, 45, 3324.
22. Chang, C. T.; Liao, B. S.; Liu, S. T. Tetrahedron Lett. 2006, 47, 9257.
23. Ollevier, T.; Nadeau, E. Org. Biomol. Chem. 2007, 5, 3126.
24. Vencato, I.; Mascarenhas, Y. P.; Pilli, R. A.; Russowsky, D. J. Braz. Chem. Soc. 1992, 3, 65.
25. Bigdeli, M. A.; Nemati, F.; Mahdavinia, G. H. Tetrahedron Lett. 2007, 48, 6801.
26. Mukhopadhyay, C.; Datta, A.; Butcher, R. Y. Tetrahedron Lett. 2009, 50, 4246.
27. Wu, H.; Shen, Y.; Fan, L.-Y.; Wan, Y.; Zhang, P.; Chenand, C.-F.; Wang, W.-X. Tetrahedron 2007, 63, 2404.
28. Kidwai, M.; Jain, A.; Poddar, R.; Bhardwaj, S. Appl. Organometal. Chem. 2011, 25, 335.
29. Akiyama, T.; Matsuda, K.; Fuchibe, K. Synlett 2005, 322.
30. Kumar, V. P.; Reddy, M. S.; Narender, M.; Surendra, K.; Nageswar, Y. V. D.; Rama, Rao. K. Tetrahedron Lett. 2006, 47, 6393.
31. (a) Marchetti, L.; Levine, M. ACS Catal. 2011, 1, 1090.
32. (b) Hapiot, F.; Ponchel, A.; Tilloy, S.; Monflier, E. C. R. Chimie 2011, 14, 149.
33. (a) Hapiot, F.; Tilloy, S.; Monflier, E. Chem. Rev. 2006, 106, 767.
34. (b) Six, N.; Guerriero, A.; Landy, D.; Peruzzini, M.; Gonsalvi, L.; Hapiot, F.; Monflier, E. Catal. Sci. Technol. 2011, 1, 1347.
35. (c) Monti, S.; Koehler, G.; Grabner, G. J. Phys. Chem. 1993, 97, 13011.
36. (d) Takahashi, K. Chem. Rev. 1998, 98, 2013.
37. Reddy, M. A.; Bhanumathi, N.; Rama Rao, K. Chem. Commun. 2001, 1974.
38. (a) Suresh, P.; Annalakshmi, S.; Pitchumani, K. Tetrahedron 2007, 63, 4959.
39. (b) Annalakshmi, S.; Pitchumani, K. Eur. J. Org. Chem. 2006, 1034.
40. (c) Durai Manickam, M. C.; Annalakshmi, S.; Pitchumani, K.; Srinivasan, C. Org. Biomol. Chem. 2005, 3, 1008.
41. (d) Kanagaraj, K.; Pitchumani, K. Tetrahedron Lett. 2010, 51, 3312.
42. (a) Kanagaraj, K.; Suresh, P.; Pitchumani, K. Org. Lett. 2010, 12, 4070.
43. (b) Suresh, P.; Pitchumani, K. Tetrahedron Asymmetry 2008, 19, 2037.
44. (a) Molecular Encapsulation: Organic Reactions in Constrained Systems; Brinker, U. H.; Mieusset, J. L., Eds.; Wiley: Chichester, 2010, 48.
45. (b) Siegel, B.; Breslow, R. J. Am. Chem. Soc. 1975, 97, 6869.
46. Choudhury, L. H.; Parvin, T. Tetrahedron 2011, 67, 8213.
47. Ollevier, T.; Nadeau, E. J. Org. Chem. 2004, 69, 9292.
48. Ranu, B. C.; Samanta, S.; Guchhait, S. K. Tetrahedron 2002, 58, 983.