Intramolecular photocycloaddition of a tethered bis-2,3-dihydro-4-pyridone: Stereochemistry and reactivity of the cycloadduct

Tetrahedron Letters

Volumn 39, Issue 3-4, 1998, Pages 187-190

  Comins, Daniel L ^a   Lee, Yong Sup ^a   Boyle, Paul D ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 DIHYDRO 4 PYRIDONE; HETEROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; DIASTEREOISOMER; DIMERIZATION; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032518649     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10520-2     Document Type: Article

References (20)

1. 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.; Chen, X. Tetrahedron Lett. 1995, 36, 9141.
3. (c) Comins, D. L.; Joseph, S. P.; Peters, D. D. Tetrahedron Lett. 1995, 36, 9449.
4. (d) Comins, D. L.; Joseph, S. P.; Zhang, Y. Tetrahedron Lett. 1996, 37, 793.
5. (e) Comins, D. L.; Guerra-Weltzien, L. Tetrahedron Lett. 1996, 37, 3807.
6. (f) Comins, D. L.; Chen, X.; Joseph, S. P. Tetrahedron Lett. 1996, 37, 9275.
7. (g) Comins, D. L.; Chen, X.; Morgan, L. A. J. Org. Chem. 1997, in press.
8. 2. (a) Guerry, P.; Neier, R. Chimia 1987, 41, 341.
9. (b) Guerry, P.; Neier, R. J. Chem. Soc., Chem. Commun. 1989, 1727.
10. (c) Guerry, P.; Blanco, P.; Brodbeck, H.; Pasteris, O.; Neier, R. Helv. Chem. Acta. 1991, 74, 163.
11. 3. Comins, D. L.; Zheng, X. J. Chem. Soc., Chem. Commun. 1994, 2681.
12. 4. Adamson, G.; Beckwith, A. L. J.; Kaufmann, M.; Willis, A. C. J. Chem. Soc., Chem. Commun. 1995, 1783.
13. 5. Cameron, T. S.; Cordes, R. E.; Pinto, B. M.; Szarek, W. A. Can. J. Chem. 1981, 59, 3136.
14. 6. Johnson, B. L.; Kitahara, Y.; Weakley, J. R.; Keana, J. F. W. Tetrahedron Lett. 1993, 34, 5555.
15. 7. Comins, D. L.; Joseph, S. J.; Goehring, R. R. J. Am. Chem. Soc. 1994, 116, 4719.
16. w = 0.053. Structure solved by SIR92, NRCVAX program package used for all other crystallographic calculations. All non-hydrogen atoms refined anisotropically, hydrogens atoms included at idealized positions. The authors kindly thank Dr. P. S. White of UNC-CH for the low temperature data set.
17. w = 0.051. Structure solved by SIR92, NRCVAX program package used for all other crystallographic calculations. All non-hydrogen atoms refined anisotropically, hydrogens atoms were allowed to ride on parent carbon atom.
18. 10. Atomic co-ordinates, bond lengths and angles, and displacement parameters have been deposited with the Cambridge Crystallographic Data Centre.
19. 11. PCMODEL 5.03; Serena Software, Box 3076, Bloomington, IN 47402.
20. 12. Spartan 4.1; Wavefunction, Inc., 18401 Von Karman #370, Irvine, CA 92715.