C-3 acetoxylation of N-acyl-2,3-dihydro-4-pyridones

Tetrahedron Letters

Volumn 39, Issue 32, 1998, Pages 5693-5696

  Comins, Daniel L ^a   Stolze, David A ^a   Thakker, Paresh ^a   McArdle, Cheryl L ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; N ACYL 2 ALKYL 2,3 DIHYDRO 4 PYRIDONE DERIVATIVE; PYRIDONE DERIVATIVE; TOLUENE; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; HYDROXYLATION; OXIDATION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032490887     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01195-2     Document Type: Article

References (24)

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2. (b) Comins, D. L.; Guerra-Weltzien, L. Tetrahedron Lett. 1996, 37, 3807 and references cited therein.
3. 2. (a) Comins, D. L.; Joseph, S. P.; Chen, X. Tetrahedron Lett. 1995, 36, 9141.
4. (b) Comins, D. L.; Joseph, S. P.; Peters, D. D. Tetrahedron Lett. 1995, 36, 9449.
5. (c) Comins, D. L.; Joseph, S. P.; Zhang, Y. Tetrahedron Lett. 1996, 37, 793.
6. (d) Comins, D. L.; Zhang, Y. J. Am. Chem. Soc. 1996, 118, 12248.
7. (e) Comins, D. L.; Chen, X.; Joseph, S. P. Tetrahedron Lett. 1996, 37, 9275.
8. 3. (a) Comins, D. L.; Joseph, S. P. In Advances in Nitrogen Heterocycles; Moody, C. J., Ed.; JAI Press Inc.: Greenwich, CT, 1996; Vol. 2, pp. 251-294.
9. (b) Comins, D. L.; Joseph, S. P.; Hong, H.; Alawar, R. S.; Foti, C. J.; Zhang, Y.; Chen, X.; LaMunyon, D. H.; Guerra-Weltzien, M. Pure and Applied Chem. 1997, 69, 477.
10. (c) Comins, D. L.; Chen, X.; Morgan, L. A. J. Org. Chem. 1997, 62, 7435.
11. (d) Comins, D. L.; LaMunyon, D. H.; Chen, X. J. Org. Chem. 1997, 62, 8182.
12. 4. For leading references, see: (a) Johns, B. A.; Pan, Y. T.; Elbein, A. D.; Johnson, C. R. J. Am. Chem. Soc. 1997, 119, 4856
13. (b) Nishimura, Y. In Studies in Natural Products Chemistry, Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1992, Vol. 10, pp. 495-583.
14. 5. (a) Review: Demir, A. S.; Jeganathan, A. Synthesis 1992, 235-247.
15. (b) Davis, F. A.; Chen, B.-C. Chem. Rev. 1992, 92, 919-934.
16. 6. Fang, F. G.; Prato, M.; Kim, G.; Danishefsky, S. J. Tetrahedron Lett. 1989, 30, 3625.
17. 7. Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: New York, 1983; Chapter 6.
18. 8. Brown, J. D.; Foley, M. A.; Comins, D. L. J. Am. Chem. Soc. 1988, 110, 7445.
19. 9. Comins, D. L.; Zeller, E. Tetrahedron Lett. 1991, 32, 5889.
20. 10. Midland, M. M.; Tramontano, A.; Cable, J. R. J. Org. Chem. 1980, 45, 28.
21. 3). The 2S diastereomer exhibits a singlet at 7.7 ppm, whereas the vinylic proton of the 2R isomer is found at 7.3 ppm.
22. 12. An asymmetric synthesis of (+)-9 has been reported; however, the absolute configuration was misassigned. Waldmann, H.; Braun, M. J. Org. Chem. 1992, 57, 4444.
23. 13. (a) Comins, D. L.; Salvador, J. M. J. Org. Chem. 1993, 58, 4656.
24. (b) (+)-and (-)-TCC alcohols are available from Aldrich Chemical Company.