Use of acylhydrazones as electrophiles in Mannich-type reactions, β-lactam, pyrazolidinone, and pyrazolone synthesis

Synlett

Volumn , Issue 9, 1998, Pages 1019-1021

  Kobayashi, Shu ^a,b,c   Furuta, Takayuki ^b   Sugita, Kasumi ^a,b,c   Oyamada, Hidekazu ^a,b,c  

^a UNIVERSITY OF TOKYO   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^c TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000290208     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1843     Document Type: Article

References (39)

1. Selected examples using hydrazones as electrophiles or equivalents are as follows. As far as we know, there have been no examples of Lewis acid-mediated reactions of hydrazones with nucleophiles. (a) Kodata, I.; Park, J.-Y.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1996, 841.
2. (b) Enders, D.; Ward, D.; Adam, J.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 981.
3. (c) Denmark, S. E.; Weber, T.; Piotrowski, D. W. J. Am. Chem. Soc. 1987, 109, 2224.
4. (d) Enders, D.; Schubert, H.; Nubling, C. Angew. Chem., Int. Ed. Engl. 1986, 25, 1109.
5. (e) Claremon, D. A.; Lumma, P. K.; Phillips, B. T. J. Am. Chem. Soc. 1986, 108, 8265.
6. (f) Takahashi, H.; Tomita, K.; Otomasu, H. J. Chem. Soc., Chem. Comm. 1979, 668.
7. In a pioneering work, rhodium-catalyzed enantioselective hydrogenation of acylhydrazones derived from ketones was reported. Burk, M. J.; Feaster, J. E. J. Am. Chem. Soc. 1992, 114, 6266.
8. Oyamada, H.; Kobayashi, S. Synlett 1998, 249.
9. (a) Thorn, K. F., US Patent 3615169 (1971); CA 1972, 76, 5436a.
10. (b) Kobayashi, S.; Hachiya, I.; Araki M.; Ishitani, H. Tetrahedron Lett. 1993, 34, 3755.
11. (c) Kobayashi, S. Synlett 1994, 689.
12. It has been shown that rare earth inflates are excellent catalysts for the catalytic activation of imine and related compounds, while most Lewis acids are decomposed or deactivated in the presence of basic nitrogen atoms. For example, (a) Kobayashi, S.; Busujima, T.; Nagayama, S. J. Chem. Soc., Chem. Commun. 1998, 19.
13. (b) Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1997, 119, 10049.
14. (c) Kobayashi, S.; Akiyama, R.; Kawamura, M.; Ishitani, H. Chem. Lett. 1997, 1039.
15. (d) Kobayashi, S.; Ishitani, H.; Ueno, M. Synlett 1997, 115.
16. 3 in a preliminary experiment.
17. It is also known that the imines derived from α,β-unsaturated aldehydes are often difficult to prepare due to their instability.
18. (a) Kleinman, E. F. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Chapter 4.1. Vol. 2, Pergamon Press, Oxford, 1991, 893.
19. (b) Tramontini, M.; Angiolini, L. "Mannich Bases, Chemistry and Uses," CRC Press, Boca Raton 1994, p. 106.
20. Other improved methods, see for example, (a) Danishefsky, S. J.; Kitahara, T.; McKee, R.; Schuda, P. F. J. Am. Chem. Soc. 1976, 98, 6715.
21. (b) Danishefsky, S. J.; Prisbylla, M.; Lipisko, B. Tetrahedron Lett. 1980, 21, 805.
22. (c) Seebach, D.; Betschart, C.; Schiess, M. Helv. Chim. Acta 1984, 67, 1593.
23. (d) Wada, M.; Nishihara, Y.; Akiba, K.-y. Tetrahedron Lett. 1984, 25, 5405.
24. (e) Katritzky, A. R.; Rachwal, S; Hitchins, G. J. Tetrahedron 1991, 47,2683.
25. (f) Katritzky, A. R.; Lan, X. Chem. Soc. Rev. 1994, 363.
26. Ojima I.; Inaba, S.; Yoshida, K. Tetrahedron Lett. 1977, 3643.
27. (a) Guanti, G.; Narisano, E.; Banfi, L. Tetrahedron Lett. 1987, 28, 4331.
28. (b) Mukaiyama, T.; Kashiwagi, K.; Matsui, S. Chem. Lett. 1989, 1397.
29. (c) Mukaiyama, T.; Akamatsu, H.; Han, J. S. Chem Lett. 1990, 889.
30. (d) Onaka, M.; Ohno, R.; Yanagiya, N.; Izumi, Y. Synlett 1993, 141.
31. (e) Ishihara, K.; Hanaki, N.; Funahashi, M.; Miyata, M.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1721.
32. (f) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233.
33. These problems have recently been overcome by using three-component coupling reactions of aldehydes, amines, and silyl enolates using a lanthanide triflate as a catalyst. Kobayashi, S.; Araki, M.; Yasuda, M. Tetrahedron Lett. 1995, 36, 5773.
34. Alexakis, A.; Lensen, N.; Mangeney, P. Synlett 1991, 625.
35. Cf. Seebach, D.; Wykypiel, W. Synthesis 1979, 423. See also, Ref. 1 (c).
36. 3) δ 17.1, 22.46, 22.51, 23.1, 25.8, 37.9, 50.6, 67.6, 125.50, 125.55, 125.60, 125.65, 127.6, 133.7, 150.7, 164.3, 176.5.
37. The structure was confirmed by X-ray analysis of the corresponding N-benzoyl derivative.
38. 2O (M+) 170.1419, found 170.1423.
39. Cf. Overman, L. E.; Rogers, B. N.; Tellew, J. E.; Trenkle, W. C. J. Am. Chem. Soc. 1997, 119, 7159.