TMSC1-promoted transition metal-catalyzed aza-Michael reactions of chalcones with carbamates

Synthesis

Volumn , Issue 13, 2004, Pages 2191-2195

  Xu, Li Wen ^a   Xia, Chun Gu ^a  

^a LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

Aza michael reaction; Carbamate; Conjugate addition; Enone; TMSC1; Transition metal

Indexed keywords

CATALYST ACTIVITY; SILICON COMPOUNDS;

AZA-MICHAEL REACTIONS; CHALCONES;

TRANSITION METALS;

CARBAMIC ACID DERIVATIVE; CHALCONE DERIVATIVE; CHLOROTRIMETHYLSILANE; HETEROCYCLIC COMPOUND; TRANSITION ELEMENT;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; DRUG CONJUGATION; MICHAEL ADDITION; REACTION ANALYSIS;

EID: 4544233152     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-829197     Document Type: Article

References (55)

1. (a) Drury, W. J.; Ferraris, D.; Cox, C.; Young, B.; Leckta, T. J. Am. Chem. Soc. 1998, 120, 11006.
2. (b) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474.
3. (c) Abele, S.; Seebach, D. Eur. J. Org. Chem. 2000, 6, 1.
4. (d) Varala, R.; Alam, M. M.; Adapa, S. Synlett 2003, 720.
5. (e) Fringuelli, F.; Pizzo, F.; Rucci, M.; Vaccaro, L. J. Org. Chem. 2003, 68, 7041.
6. (f) Duursma, A.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc 2003, 125, 3700.
7. (g) Gnad, F.; Reiser, O. Chem. Rev. 2003, 103, 1603.
8. (a) Gaunt, M. J.; Spencer, J. B. Org. Lett. 2001, 3, 25.
9. (b) Wabnitz, T. C.; Spencer, J. B. Tetrahedron Lett. 2002, 43, 3891.
10. (c) Kobayashi, S.; Kakumoto, K.; Sugiura, M. Org. Lett. 2002, 4, 1319.
11. (d) Jin, X. L.; Sugihara, H.; Daikai, K.; Tateishi, H.; Jin, Y. Z.; Furuno, H.; Inanaga, J. Tetrahedron 2002, 58, 8321.
12. (e) Xu, L. W.; Xia, C. G.; Li, J. W.; Zhou, S. L. Synlett 2003, 2246.
13. (f) Sibi, M. P.; Prabagaran, N.; Ghorpade, S. G.; Jasperse, C. P. J. Am. Chem. Soc. 2003, 125, 11796.
14. (g) Xu, L. W.; Li, J. W.; Xia, C. G.; Zhou, S. L.; Hu, X. X. Synlett 2003, 2425.
15. (h) Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 16178.
16. (a) Enders, D.; Muller, S. F.; Raabe, G. Angew. Chem. Int. Ed. 1999, 38, 195.
17. (b) Gaunt, M. J.; Spencer, J. B. Org. Lett. 2001, 3, 25.
18. (c) Enders, D.; Wallert, S. Synlett 2002, 304.
19. (d) Sani, M.; Bruche, L.; Chiva, G.; Fustero, S.; Piera, J.; Volonterio, A.; Zanda, M. Angew. Chem. Int. Ed. 2003, 42, 2060.
20. (e) Volonterio, A.; Zanda, M. Tetrahedron 2003, 44, 8549.
21. (f) Xu, L. W.; Li, J. W.; Xia, C. G. New J. Chem. 2004, 183.
22. (g) Xu, L. W.; Li, L.; Xia, C. G.; Zhou, S. L.; Li, J. W. Tetrahedron Lett. 2004, 45, 1219.
23. (a) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon: New York, 1992, 114.
24. (b) Perez, M.; Pleixates, R. Tetrahedron 1995, 51, 8355.
25. (c) Asao, N.; Shimada, T.; Sudo, T.; Tsukada, N.; Yazawa, K.; Gyoung, Y. S.; Yamamoto, Y. J. Org. Chem. 1997, 62, 6274; and references cited therein.
26. (d) Bull, S. D.; Davies, S. G.; Delgado-Ballester, S.; Fenton, G.; Kelly, P. M.; Smith, A. D. Synlett 2000, 1257.
27. (e) Fadini, L.; Togni, A. Chem. Commun. 2003, 30.
28. (f) Sani, M.; Bruche, L.; Chiva, G.; Fustero, S.; Fiera, J.; Volonterio, A.; Zanda, M. Angew. Chem. Int. Ed. 2003, 42, 2060.
29. Matsubara, S.; Yoshioka, M.; Utimoto, K. Chem. Lett. 1994, 827.
30. Loh, T. P.; Wei, L. L. Synlett 1998, 975.
31. (a) Kawatsura, M.; Hartwig, J. F. Organometallics 2001, 20, 1960.
32. (b) Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033.
33. (c) Zhuang, W.; Hazell, R. G.; Jørgensen, K. A. Chem. Commun. 2001, 1240.
34. (d) Sibi, M. P.; Liu, M. Org. Lett. 2000, 2, 3393.
35. (e) Sibi, M. P.; Shay, J. J.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 1998, 120, 6615.
36. Bartoli, G.; Bosco, M.; Marcantoni, E.; Pertrini, M.; Sambri, L.; Torregiani, E. J. Org. Chem. 2001, 66, 9052.
37. Srivastava, N.; Banik, B. K. J. Org. Chem. 2003, 68, 2109.
38. (a) Wabnitz, T. C.; Yu, J. Q.; Spencer, J. B. Synlett 2003, 1070.
39. (b) Wabnitz, T. C.; Spencer, J. B. Org. Lett. 2003, 5, 2141.
40. (c) Xu, L. W.; Li, L.; Xia, C. G.; Zhou, S. L.; Li, J. W.; Hu, X. X. Synlett 2003, 2337.
41. (d) Xu, L. W.; Xia, C. G.; Hu, X. X. Chem. Commun. 2003, 2570.
42. (e) Enders, D.; Wallert, S.; Runsink, J. Synthesis 2003, 1856.
43. (a) Christoffers, J.; Oertling, H. Tetrahedron 2000, 56, 1339.
44. (b) Christoffers, J. Eur. J. Org. Chem. 1998, 1259.
45. (c) Christoffers, J. Chem. Commun. 1997, 943.
46. (d) Kim, S. S.; Nehru, K.; Kim, S. S.; Kim, D. W.; Jung, H. C. Synthesis 2002, 2484.
47. Recent work: (a) TMSCl as a scavenger: Fischer, S.; Groth, U.; Jeske, M.; Schulz, T. Synlett 2002, 1922. (b) Chlorotrimethylsilane as additive: Ito, T.; Ishino, Y.; Mizuno, T.; Iswkawa, A.; Kobayashi, J. Synlett 2002, 2116. (c) Johnson, C. R.; Marren, T. J. Tetrahedron Lett. 1987, 28, 27. (d) Lee, P. H.; Lee, H. A. K.; Sung. S.; Kim, S. Tetrahedron Lett. 2001, 42, 37. (e) Bunch, L.; Krogsgaard-Larsen, P.; Madsen, U. Synthesis 2002, 31. (f) Bandini, M.; Fagioli, M.; Melloni, A.; Umani-Ronchi, A. Synthesis 2003, 397.
48. Recent work: (a) TMSCl as a scavenger: Fischer, S.; Groth, U.; Jeske, M.; Schulz, T. Synlett 2002, 1922. (b) Chlorotrimethylsilane as additive: Ito, T.; Ishino, Y.; Mizuno, T.; Iswkawa, A.; Kobayashi, J. Synlett 2002, 2116. (c) Johnson, C. R.; Marren, T. J. Tetrahedron Lett. 1987, 28, 27. (d) Lee, P. H.; Lee, H. A. K.; Sung. S.; Kim, S. Tetrahedron Lett. 2001, 42, 37. (e) Bunch, L.; Krogsgaard-Larsen, P.; Madsen, U. Synthesis 2002, 31. (f) Bandini, M.; Fagioli, M.; Melloni, A.; Umani-Ronchi, A. Synthesis 2003, 397.
49. Recent work: (a) TMSCl as a scavenger: Fischer, S.; Groth, U.; Jeske, M.; Schulz, T. Synlett 2002, 1922. (b) Chlorotrimethylsilane as additive: Ito, T.; Ishino, Y.; Mizuno, T.; Iswkawa, A.; Kobayashi, J. Synlett 2002, 2116. (c) Johnson, C. R.; Marren, T. J. Tetrahedron Lett. 1987, 28, 27. (d) Lee, P. H.; Lee, H. A. K.; Sung. S.; Kim, S. Tetrahedron Lett. 2001, 42, 37. (e) Bunch, L.; Krogsgaard-Larsen, P.; Madsen, U. Synthesis 2002, 31. (f) Bandini, M.; Fagioli, M.; Melloni, A.; Umani-Ronchi, A. Synthesis 2003, 397.
50. Recent work: (a) TMSCl as a scavenger: Fischer, S.; Groth, U.; Jeske, M.; Schulz, T. Synlett 2002, 1922. (b) Chlorotrimethylsilane as additive: Ito, T.; Ishino, Y.; Mizuno, T.; Iswkawa, A.; Kobayashi, J. Synlett 2002, 2116. (c) Johnson, C. R.; Marren, T. J. Tetrahedron Lett. 1987, 28, 27. (d) Lee, P. H.; Lee, H. A. K.; Sung. S.; Kim, S. Tetrahedron Lett. 2001, 42, 37. (e) Bunch, L.; Krogsgaard-Larsen, P.; Madsen, U. Synthesis 2002, 31. (f) Bandini, M.; Fagioli, M.; Melloni, A.; Umani-Ronchi, A. Synthesis 2003, 397.
51. Recent work: (a) TMSCl as a scavenger: Fischer, S.; Groth, U.; Jeske, M.; Schulz, T. Synlett 2002, 1922. (b) Chlorotrimethylsilane as additive: Ito, T.; Ishino, Y.; Mizuno, T.; Iswkawa, A.; Kobayashi, J. Synlett 2002, 2116. (c) Johnson, C. R.; Marren, T. J. Tetrahedron Lett. 1987, 28, 27. (d) Lee, P. H.; Lee, H. A. K.; Sung. S.; Kim, S. Tetrahedron Lett. 2001, 42, 37. (e) Bunch, L.; Krogsgaard-Larsen, P.; Madsen, U. Synthesis 2002, 31. (f) Bandini, M.; Fagioli, M.; Melloni, A.; Umani-Ronchi, A. Synthesis 2003, 397.
52. Recent work: (a) TMSCl as a scavenger: Fischer, S.; Groth, U.; Jeske, M.; Schulz, T. Synlett 2002, 1922. (b) Chlorotrimethylsilane as additive: Ito, T.; Ishino, Y.; Mizuno, T.; Iswkawa, A.; Kobayashi, J. Synlett 2002, 2116. (c) Johnson, C. R.; Marren, T. J. Tetrahedron Lett. 1987, 28, 27. (d) Lee, P. H.; Lee, H. A. K.; Sung. S.; Kim, S. Tetrahedron Lett. 2001, 42, 37. (e) Bunch, L.; Krogsgaard-Larsen, P.; Madsen, U. Synthesis 2002, 31. (f) Bandini, M.; Fagioli, M.; Melloni, A.; Umani-Ronchi, A. Synthesis 2003, 397.
53. (a) Nakamura, E.; Matsuzawa, S.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1986, 27, 4092.
54. (b) Horiguchi, Y.; Matsuzawa, S.; Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1986, 27, 4025.
55. (c) Matsuzawa, S.; Horiguchi, Y.; Nakamura, E.; Kuwajima, I. Tetrahedron 1989, 45, 394.