Diastereoselective Michael addition of organolithium reagents to chiral α,β-unsaturated selenoamide

Synlett

Volumn , Issue 6, 1998, Pages 619-620

  Murai, Toshiaki ^a   Mori, Toshihiro ^a   Kato, Shinzi ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000700724     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1749     Document Type: Article

References (20)

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3. For examples: (a) Costa, J. S.; Dias, A. G.; Anholeto, A. L.; Monteiro, M. D.; Patrocinio, V. L.; Costa, P. R. R. J. Org. Chem. 1997, 62, 4002.
4. (b) Asao, N.; Shimada, T.; Sudo, T.; Tsukada, N.; Yazawa, K.; Gyoung, Y. S.; Uyehara, T.; Yamamoto, Y. J. Org. Chem. 1997, 62, 6274.
5. Murai, T.; Ezaka, T.; Ichimiya, T.; Kato, S. Synlett 1997, 775.
6. (a) Guziec, F. S. Jr.; Guziec, L. 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. (b) 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. (c) 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.
9. (d) Ishihara, H.; Yoshimi, M.; Hara, N.; Ando, H.; Kato, S. Bull. Chem. Soc. Jpn. 1990, 63, 835.
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11. (f) Murai, T.; Kakami, K.; Hayashi, A.; Komuro, T.; Takada, H.; Fujii, M.; Kanda, T.; Kato, S. J. Am. Chem. Soc. 1997, 119, 8592 and references cited therein.
12. (a) Wu, R.; Hernández, G.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. J. Chem. Soc., Chem. Commun. 1996, 1125.
13. (b) Wu, R.; Silks, L. A.; Odom, J. D.; Dunlap, R. B. Spectroscopy 1996, 11, 37 and references cited therein.
14. 3) δ 559.9.
15. Schmid, C. R.; Bryant, J. D. Org. Synth. 1993, 72, 6.
16. 3) δ -5.8, -5.7, 13.1, 25.7, 33.6, 37.2, 45.8, 62.2, 80.5, 117.6, 134.7, 178.7.
17. Despite the potential utility of azaselenoacetals their syntheses are rare: Kennewell, P. D.; Westwood, R.; Westwood, N. J. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R.: Meth-Cohn, O., Rees, C. W., Eds.; Pergamon: Oxford, 1995; Vol. 4, p 909.
18. 2 (1:1) as eluent to give selenoamide 4 (65%).
19. Shimada, K.; Akimoto, S.; Itoh, H.; Nakamura, H.; Takikawa, Y. Chem. Lett. 1994, 1743.
20. Nubbemeyer, U. J. Org. Chem. 1995, 60, 3773.