Synthesis of α,β-Unsaturated Selenoamides by the Condensation Reaction of Lithium Eneselenolate Generated from Selenoacetamide with Aldehydes

Synlett

Volumn 1997, Issue 7, 1997, Pages 775-776

  Murai, Toshiaki ^a   Ezaka, Tatsuya ^a   Ichimiya, Toshio ^a   Kato, Shinzi ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000677885     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-5781     Document Type: Article

References (23)

1. (a) Perlmutler, P. In Conjugate Addition Reactions in Organic Synthesis; Baldwin, J. E., Ed.; Pergamon: Oxford, 1992.
2. (b) In Organocopper Reagents: Taylor, R. J. K. Ed.; Oxford University Press: Oxford, 1994.
3. Dell, C. P. In Comprehensive Organic functional Group Transformations, Vol. 5; Katritzky, A. R.; Meth-Cohn, O.; Rees, C. W., Eds.; Pergamon: Oxford, 1995; p 624.
4. (a) Ogawa, A.; Sonoda, N. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Ed.; Pergamon: Oxford, 1991; Vol. 6, p 476.
5. (b) Ogawa, A.; Sonoda, N. Rev. Heteroatom Chem. 1994, 10, 43.
6. (c) Guziec, F. S. Jr.; Guziec, E. J. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R.: Meth-Cohn, O., Rees, C. W., Eds.; Pergamon: Oxford, 1995; Vol. 3. p 381.
7. (d) Ishii A.; Nakayama, J. In Comprehensive Organic Functional Group Transformations: Katritzky, A. R.: Meth-Cohn, O., Rees, C. W., Eds.; Pergamon: Oxford, 1995; Vol. 5, p 505.
8. Li, G. M.; Segi, M.; Nakajima, T. Tetrahedron Lett. 1992, 33, 3515.
9. (a) Fischer, H.; Tiriliomis, A.; Gerhing, U.; Huber, B.; Müller, G. J. Chem. Soc., Chem. Commun. 1987, 559.
10. (b) Fischer, H.; Gerbing, U.; Tiriliomis, A.; Müller, G.; Huber, B.; Riede, J.; Hofmann, J.; Burger, P. Chem. Ber. 1988, 121, 2095.
11. (c) Fischer, H.; Hofmann, J.; Gerbing, U.; Tiriliomis, A. J. Organomet. Chem. 1988, 358, 229.
12. (d) Fischer, H.; Treier, K.; Hofmann, J. J. Organomet. Chem. 1990, 384, 305.
13. Takikawa, Y.; Watanabe, H.; Sasaki, R.; Shimada, K. Bull. Chem. Soc. Jpn. 1994, 67, 876.
14. Shimada, K.; Akimoto, S.; Itoh, H.; Nakamura, H.; Takikawa, Y. Chem. Lett. 1994, 1743.
15. Murai, T.; Ezaka, T.; Niwa, N.; Kanda, T.; Kato, S. Synlett 1996, 865.
16. 2 as eluent to give α,β-unsaturated selenoamide 3a (75%).
17. 21NSe: C, 57.77; H. 7.83. Found: C, 57.58; H, 8.03.
18. 77Se NMR spectrum is at 611.6 ppm, see also ref. 12.
19. Duddeck, H. Progress in NMR Spectroscopy 1995, 27, 1.
20. Sukhai, R. S.; Brandsma, L. Synthesis 1979, 455.
21. Woodhury, R. P.; Rathke, M. W. J. Org. Chem. 1977, 42, 1688.
22. Tamaru, Y.; Harada, T.; Nishi, S.; Mizutani, M.; Hioki, T.; Yoshida, Z. J. Am. Chem. Soc. 1980, 102, 7806.
23. Tamaru, Y.; Harada, T.; Iwamoto, H.; Yoshida, Z. J. Am. Chem. Soc. 1978, 100, 5221.