Stereoselective synthesis of β-amino ketones via direct Mannich-type reactions, catalyzed with ZrOCl2·8H2O under solvent-free conditions

European Journal of Organic Chemistry

Volumn , Issue 22, 2006, Pages 5152-5157

  Eftekhari Sis, Bagher ^a   Abdollahifar, Amir ^a   Hashemi, Mohammed M ^a   Zirak, Maryam ^b  

^a SHARIF UNIVERSITY OF TECHNOLOGY   (Iran)

^b UNIVERSITY OF TABRIZ   (Iran)

Author keywords

amino ketones; Direct Mannich type reaction; Solvent free conditions; Zirconium oxychloride

Indexed keywords

EID: 33751327325     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600493     Document Type: Article

References (62)

1. a) R. W. Armstrong, A. P. Combs, P. A. Tempest, S. D. Brown, T. A. Keating, Acc. Chem. Res. 1996, 29, 123-131;
2. b) S. Kobayashi, Chem. Soc. Rev. 1999, 28, 1-26;
3. c) L. Weber, K. Illgen, M. Almstetter, Synlett 1999, 366-374;
4. d) S. L. Dax, J. J. McNally, M. A. Youngman, Curr. Med. Chem. 1999, 6, 255-270;
5. e) A. Dömling, I. Ugi, Angew. Chem. Int. Ed. 2000, 39, 3168-3210;
6. f) S. L. Schreiber, Science 2000, 287, 1964-1969;
7. g) H. Bienayme, C. Hulme, G. Oddon, P. Schmitt, Chem. Eur. J. 2000, 6, 3321-3329;
8. h) S. P. Lal, R. I. Christopherson, C. G. dos Remedios, Drug Discovery Today 2002, 7, 143-149;
9. i) L. Weber, Curr. Med. Chem. 2002, 9, 1241-1253;
10. j) G. Balme, M. N. Bossharth, Eur. J. Org. Chem. 2003, 4101-4111;
11. k) A. Jacobi Von Wangelin, H. Neumann, D. Gördes, S. Klaus, A. Strübing, M. Beller, Chem. Eur. J. 2003, 9, 4286-4294.
12. M. Arend, B. Westermann, N. Risch, Angew. Chem. Int. Ed. 1998, 37, 1044-1070.
13. For comprehensive reviews see: a) M. Tramontini, L. Angiolini, Mannich-Bases, Chemistry and Uses; CRC, Boca Raton, Florida, 1994, and references cited therein;
14. b) R. A. Volkmann, in: Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, vol. 1, p. 355 and references cited therein.
15. a) N. Azizi, L. Torkiyan, M. R. Saidi, Org. Lett. 2006, 8, 2079-2082;
16. b) Y.-S. Wu, J. Cai, Z.-Y. Hu, G.-X. Lin, Tetrahedron Lett. 2004, 45, 8949-8952;
17. c) K. Manabe, S. Kobayashi, Org. Lett. 1999, 1, 1965-1967;
18. d) S. Iimura, D. Nobutou, K. Manabe, S. Kobayashi, Chem. Commun. 2003, 1644-1645;
19. e) B. C. Ranu, S. Samanta, S. K. Guchhait, Tetrahedron 2002, 58, 983-988;
20. f) T.-P. Loh, L.-L. Wei, Tetrahedron Lett. 1998, 39, 323-326.
21. For enantioselective Mannich reactions see: g) I. Ibrahem, W. Zou, M. Engqvist, Y. Xu, A. Cordova, Chem. Eur. J. 2005, 11, 7024-7029;
22. h) A. J. A. Cobb, D. M. Shaw, S. V. Ley, Synlett 2004, 558-560;
23. i) I. Ibrahem, J. Casas, A. Crdova, Angew. Chem. Int. Ed. 2004, 43, 6528-6531.
24. For reviews of catalytic Mannich reactions see: j) S. Kobayashi, M. Ueno, in: Comprehensive Asymmetric Catalysis, Supplement, Springer, Berlin, 2004, vol. 1, pp. 143;
25. k) A. Cordova, Acc. Chem. Res. 2004, 37, 102-112.
26. J. P. Riley, R. Chester, Introduction to Marine Chemistry, Academic Press, New York, 1971.
27. F. Farnworth, S. L. Jones, I. McAlpine, Speciality Inorganic Chemicals Special publication, no. 40, Royal Society of Chemistry, London, 1980.
28. P. J. Moles, http://www.zrchem.com.
29. a) R. Lenarsic, M. Kocevar, S. Polanc, J. Org. Chem. 1999, 64, 2558-2563;
30. b) H. Firouzabadi, N. Iranpoor, B. Karimi, Synlett 1999, 319-320;
31. c) K. P. Chary, G. H. Mohan, D. S. Iyengar, Chem. Lett. 1999, 12, 1339-1340;
32. d) K. P. Chary, S. R. Ram, G. H. Mohan, D. S. Iyengar, Synlett 2000, 683-685;
33. e) B. Karimi, H. Seradj, Synlett 2000, 805-806;
34. f) C. Tsuji, E. Miyazawa, T. Sakamoto, Y. Kikugawa, Synth. Commun. 2002, 32, 3871-3879;
35. g) G. Smitha, S. Patnaik, C. S. Reddy, Synthesis 2005, 711-713;
36. h) A. K. Chakraborti, A. Kondaskar, Tetrahedron Lett. 2003, 44, 8315-8319;
37. i) M. Shi, S. C. Cui, Q. J. Li, Tetrahedron 2004, 60, 6679-6684;
38. j) Spotlight: U. Bora, Synlett 2003, 1073-1074;
39. k) H. W. Heine, D. L. Cottle, H. L. Van Mater, J. Am. Chem. Soc. 1946, 68, 524-524;
40. l) T. Poll, G. Helmchen, B. Bauer, Tetrahedron Lett. 1984, 25, 2191-2194;
41. m) D. A. Evans, K. T. Chapman, J. Bisaha, J. Am. Chem. Soc. 1988, 110, 1238-1256;
42. n) M. Frank-Neumann, M. Miesch, L. Gross, Tetrahedron Lett. 1990, 31, 5027-5030;
43. o) S. E. Denmark, E. J. Weber, T. M. Wilson, Tetrahedron 1989, 45, 1053-1065;
44. p) S. Itsuno, Y. Sakurai, K. Ito, Synthesis 1988, 995-996;
45. q) S. Itsuno, Y. Sakurai, K. Shimizu, K. M. Ito, J. Chem. Soc. Perkin Trans. 1 1990, 1859-1863;
46. r) K. P. Chary, R. M. Thomas, D. S. Iyengar, Indian J. Chem. Sec. B 2000, 39, 57;
47. s) D. C. Harrowven, R. F. Dainty, Tetrahedron Lett. 1996, 37, 7659-7660;
48. t) J. S. Yadav, B. V. S. Reddy, K. S. Ray, K. B. Reddy, A. R. Prasad, Synthesis 2001, 2277-2280;
49. u) S. Smitha, Ch. S. Reddy, Synthesis 2004, 834-836;
50. v) K. Ishihara, M. Nakayama, S. Ohara, H. Yamamoto, Tetrahedron 2002, 58, 8179-8188;
51. w) A. K. Chakraborti, R. Gulhane, Synlett 2004, 627-630.
52. a) A. M. Anderson, J. M. Blazek, P. Garg, B. J. Payne, R. S. Mohan, Tetrahedron Lett. 2000, 41, 1527-1530;
53. b) R. D. Crouch, C. A. Romany, A. C. Kreshock, K. A. Menconi, J. L. Zile, Tetrahedron Lett. 2004, 45, 1279-1281;
54. c) R. Ghosh, S. Maiti, A. Chakraborty, Tetrahedron Lett. 2004, 45, 6775-6778;
55. d) A. K. Chakraborti, R. Gulhane, Shivani, Synlett 2003, 1805-1808.
56. M. M. Hashemi, B. Eftekhari-Sis, A. Abdollahifar, B. Khalili, Tetrahedron 2006, 62, 672-677.
57. a) M. M. Hashemi, B. Eftekhari-Sis, B. Khalili, Z. Karimi-Jaberi, J. Braz. Chem. Soc. 2005, 16, 1082-1084;
58. b) M. M. Hashemi, B. Khalili, B. Eftekhari-Sis, J. Chem. Res. 2005, 484-485.
59. a) Y. Hayashi, T. Urushima, M. Shoji, T. Uchimaru, I. Shiinac, Adv. Synth. Catal. 2005, 347, 1595-1604;
60. b) T. Akiyama, J. Takaya, H. Kagoshima, Adv. Synth. Catal. 2002, 344, 338-347;
61. c) A. Yanagisawa, H. Saito, M. Harada, T. Araia, Adv. Synth. Catal. 2005, 347, 1517-1522.
62. T. Akiyama, K. Matsuda, K. Fuchibe, Synlett 2005, 322-324.