The Mukaiyama-Michael reaction of N-Acyl-2,3-dihydro-4-pyridones: Regio- and stereoselective synthesis of cis-2,6-disubstituted 1,2,5,6-tetrahydropyridines

Organic Letters

Volumn 1, Issue 7, 1999, Pages 1031-1033

  Kuethe, Jeffrey T ^a   Comins, Daniel L ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIDINE DERIVATIVE; PYRIDONE DERIVATIVE;

ARTICLE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

PYRIDINES; PYRIDONES; STEREOISOMERISM;

EID: 0033533644     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9908124     Document Type: Article

References (20)

1. (a) Fowler, F. W. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: London, 1984; Vol. 2, Part 2A, pp 365-394.
2. (b) Coutts, R. T.; Scott, J. R. Can. J. Pharm. Sci. 1971, 6, 78.
3. (c) Ferles, M.; Pliml, J. Adv. Heterocycl. Chem. 1970, 12, 43-101.
4. For some recent work and leading references, see: (a) Angle, S. R.; Breitenbucher, J. G. In Studies in Natural Products Chemistry: Stereoselective Synthesis; Atta-ur Rahman, Ed.; Elsevier: New York, 1995; Vol. 16, Part J, pp 453-502.
5. (b) Wang, C. J.; Wuonola, M. A. Org. Prep. Proced. Int. 1992, 24, 583-621.
6. (c) Waldmann, H. Synthesis 1994, 535.
7. (d) Schürer, S. C.; Blechert, S. Tetrahedron Lett. 1999, 40, 1877.
8. (e) Aahman, J.; Somfai, P. Tetrahedron Lett. 1996, 37, 2495.
9. (f) Castro, P.; Overman, L. E.; Zhang, X.; Mariano, P. S. Tetrahedron Lett. 1993, 34, 5243.
10. (a) Comins, D. L.; Joseph, S. P.; Goehring, R. R. J. Am. Chem. Soc. 1994, 116, 4719.
11. (b) Comins, D. L.; LaMunyon, D. H. Tetrahedron Lett. 1994, 35, 7343.
12. (c) Comins, D. L.; Guerra-Weltzien, L. Tetrahedron Lett. 1996, 37, 3807.
13. (d) Comins, D. L.; Kuethe, J. T.; Hong, H.; Lakner, F. J. J. Am. Chem. Soc. 1999, 121, 2651.
14. Comins, D. L.; Brown, J. D. Tetrahedron Lett. 1986, 27, 4549.
15. Saigo, K.; Osaki, M.; Mukaiyama, T. Chem. Lett 1976, 163.
16. Comins, D. L.; LaMunyon, D. H.; Chen, X. J. Org. Chem. 1997, 62, 8182 and references therein.
17. (a) Reich, H. J.; Chow, F. J. Chem. Soc., Chem. Commun. 1975, 790.
18. (b) Rémion, J.; Dumont, W.; Krief. A. Tetrahedron Lett. 1976, 17, 1385.
19. A similar radical 1,2-elimination reaction has been used with carbocyclic compounds; see: Lythgoe, B.; Waterhouse, I. Tetrahedron Lett. 1977, 18, 4223.
20. 1H NMR spectra and elemental analysis or high-resolution mass spectra.