Reactions of α,α-disubstituted selenoamides with organolithium reagents leading to unsymmetrical ketones

Tetrahedron Letters

Volumn 39, Issue 24, 1998, Pages 4329-4332

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

^a GIFU UNIVERSITY   (Japan)

Author keywords

Alkylations; Enamines; Selenium and compounds

Indexed keywords

KETONE DERIVATIVE; ORGANOSELENIUM DERIVATIVE; SELENOAMINO ACID;

ARTICLE; CHEMICAL BINDING; CHEMICAL REACTION KINETICS; DRUG SYNTHESIS; MOLECULAR INTERACTION;

EID: 0032507924     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00764-3     Document Type: Article

References (25)

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2. (b) The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S., Ed.; John Wiley & Sons: New York, 1986 and 1987; Vol. 1 and 2.
3. (c) Organoselenium Chemistry; Liotta, D., Ed.; Wiley-Interscience: New York, 1987.
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9. (e) Murai, T.; Ezaka, T.; Ichimiya, T.; Kato, S. Synlett 1997, 775.
10. 6 was not confirmed in the present reaction.
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12. (6) 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, U.K., 1995; Vol. 3, p 381.
13. (7) The reaction of an α-monosubstituted selenoamide with phenyllithium has been reported to give an enamine in a low yield, see: Sekiguchi, M.; Ogawa, A.; Fujiwara, S.; Ryu, I.; Kambe, N.; Sonoda, N. Chem. Lett. 1990, 2053.
14. (8) Whitesell, J. K.; Whitesell, M. A. Synthesis 1983, 517.
15. (9) For examples, see: (a) Wakefield, B. J. In Organolithium Methods; Academic Press: London, 1988; p 82.
16. (b) O'Neill, B. T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 1, p 397.
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19. (e) Myers, A. G.; Yang, B. H.; Chen, H.; McKinstry, L.; Kopecky, D. J.; Gleason, J. L. J. Am. Chem. Soc. 1997, 119, 6496.
20. (10) The selenoamides 1c-h were prepared by the allylation or aldol condensation of α-monosubstituted selenoamide.
21. 2O as eluent to give the corresponding unsymmetrical ketones 2.
22. (12) All new compounds gave satisfactory spectral and microanalytical data.
23. (13) Zweifel, G.; Lewis, W. J. Org. Chem. 1978, 43, 2739.
24. (14) The regio- and stereo-chemistry of the product 8 were determined by HMBC and PNOEZY spectroscopy.
25. (15) Braverman, S.; Duar, Y. J. Am. Chem. Soc. 1990, 112, 5830.