Synthesis and reactivity of N-acyl-5-(1-hydroxyalkyl)-2,3-dihydro-4-pyridones

Organic Letters

Volumn 3, Issue 5, 2001, Pages 769-771

  Comins, Daniel L ^a   Hiebel, Anne Cécile ^a   Huang, Shenlin ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIDONE DERIVATIVE;

ARTICLE; CATALYSIS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION; SYNTHESIS;

CATALYSIS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; OXIDATION-REDUCTION; PYRIDONES;

EID: 0035826387     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015529v     Document Type: Article

References (24)

1. (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.
2. (b) Comins, D. L.; Joseph, S. P. In Comprehensive Heterocyclic Chemistry, 2nd ed.; McKillop, A., Ed.; Pergamon Press: Oxford, England, 1996; Vol. 5, pp 37-89.
3. (a) Comins, D. L.; Joseph, S. P.; Goehring, R. R. J. Am. Chem. Soc. 1994, 116, 4719.
4. (b) Kuethe, J. T.; Comins, D. L. Org. Lett. 2000, 2, 855 and references therein.
5. For the synthesis of related dihydropyridones using the aza Diels-Alder reaction, see: Kirschbaum, S.; Waldmann, H. J. Org. Chem. 1998, 63, 4936 and references therein.
6. Comins, D. L. J. Heterocycl. Chem. 1999, 36, 1491 and references therein.
7. For reviews, see: (a) Ciganek, E. Org. React. 1997, 51, 201.
8. (b) Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001.
9. (c) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653.
10. Shi, M.; Jiang, J.-K.; Feng, Y.-S. Org. Lett. 2000, 2, 2397 and references therein.
11. For reviews, see: (a) Fürstner, A. Chem. Rev. 1999, 99, 991-1045.
12. (b) Wessjohann, L. A.; Scheid, G. Synthesis 1999, 1-36.
13. McCauley, J. A.; Nagasawa, K.; Lander, P. A.; Mischke, S. G.; Semones, M. A.; Kishi, Y. J. Am. Chem. Soc. 1998, 120, 7647.
14. Comins, D. L.; Joseph, S. P.; Chen, X. Tetrahedron Lett. 1995, 36, 9141.
15. 2.
16. (b) For the synthesis of α-iodo enones from the corresponding α-silyl precursors using ICl, see: Alimardanov, A.; Negishi, E. Tetrahedron Lett. 1999, 40, 3839.
17. The relative stereochemistry of the diastereomers 3 was not determined.
18. For examples of γ-hydroxyenecarbamates as unsaturated N-acyliminium ion precursors, see: (a) Kozikowski, A. P.; Park, P.-u. J. Org. Chem. 1984, 49, 1674.
19. (b) Comins, D. L.; Abdullah, A. H. Tetrahedron Lett. 1985, 26, 43.
20. (c) Comins, D. L.; Stroud, E. D. Tetrahedron Lett. 1986, 27, 1869.
21. (d) Kozikowski, A. P.; Park, P.-u J. Org. Chem. 1990, 55, 4668.
22. (e) Comins, D. L.; Killpack, M. O. J. Am. Chem. Soc. 1992, 114, 10972.
23. Luche reduction of dihydropyridones of type 1 generally gives equatorial alcohols, see: Comins, D. L.; Chung, G.; Foley, M. A. Heterocycles 1994, 37, 1121.
24. 13C NMR spectra and elemental analysis or high-resolution mass spectra.