Conformational Analysis of 4-Tetrahydropyranones: A Combined Molecular Mechanics (MM2) and ab Initio MO Study

Journal of Organic Chemistry

Volumn 58, Issue 6, 1993, Pages 1367-1371

  Gung, Benjamin W ^a   Zhu, Zhaohai ^a   Mareska, David A ^a  

^a MIAMI UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33751386527     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00058a014     Document Type: Article

References (30)

1. Danishefsky, S.; Langer, M. E. J. Org. Chem. 1985, 50, 3672.
2. Nakata, T.; Nagao, S.; Oishi, T. Tetrahedron Lett. 1985, 26, 75, and refs therein.
3. Wigfield, D. C.; Feiner, S. Can. J. Chem. 1978, 56, 789.
4. Brown, H. C.; Krishnamurthy, S. Tetrahedron. 1979, 35, 567.
5. Cieplak, A. S. J. Am. Chem. Soc. 1981, 103, 4540.
6. Cieplak, A. S.; Tait, B. D.; Johnson, C. R. J. Am. Chem. Soc. 1989, 111, 8447.
7. For a leading reference, which supports the Cieplak thesis, see: Bodepudi, V.; le Noble, W. J. J. Org. Chem. 1991, 56, 2001.
8. For a leading critic, see: Wu, Y. D.; Tucker, J. A.; Houk, K. N. J. Am. Chem. Soc. 1991, 11. 5018.
9. cf., (a) Allinger, N. L.; Chung, D. Y. J. Am. Chem. Soc. 1976, 98, 6798.
10. Allinger, N. L.; Rahman, M.; Lii, J.-H. J. Am. Chem. Soc. 1990, 112, 8293.
11. Durrette, P. L.; Horton, D. Adv. Carbohydr. Chem. Biochem. 1971, 26, 49.
12. Lemieuz, R. U. Pure Appl. Chem. 1971, 25, 527.
13. Szarek, W. A.; Horton, D. Anomeric Effects; ACS Symposium Series, No. 87; American Chemical Society: Washington, D.C., 1979.
14. de Hoog, A. J.; Buys, H. R.; Altona, C.; Havingga, E. Tetrahedron, 1969, 25, 3365.
15. Burkert, U.; Allinger, N. L. Molecular Mechanics. American Chemical Society: Washington, D.C., 1982.
16. For a discussion of the implication of anomeric effects in MM2, see: Norskov-Lauritsen, L.; Allinger, N. L. J. Comput. Chem. 1984, 5, 326.
17. For other MM2 studies of the conformations for compounds having anomeric carbons, see: (a) Navio, P. F.; Molina, J. M. J. Mol. Struct. 1990, 222, 387.
18. Entrena, A.; Gallo, M. A.; Espinosa, A.; Jaime, C.; Campos, J.; Dominguez, J. F. J. Org. Chem. 1989, 54, 6034.
19. Still, W. C. MacroModel 2.5, Columbia University.
20. For the performance of the MacroModel program in locating conformational minima, see: Saunders, M.; Houk, K. N.; Wu, Y. D.; Still, W. C.; Lipton, M.; Chang, G.; Guida, W. C. J. Am. Chem. Soc. 1990, 112, 1419.
21. Gorthey. L. A.; Vairamani. M.; Djerassi, C. J. Org. Chem., 1985, 50, 4173.
22. Bowen, J. P.; Allinger, N. L. J. Org. Chem. 1987, 52, 1830.
23. Booth, H.; Everett, J. R. J. Chem. Soc. Chem. Commun. 1976, 278.
24. Allinger, N. L.; Freiberg, L. A. J. Org. Chem., 1966, 31, 894.
25. Eliel, E. L.; Manoharan. M. J. Org. Chem., 1981, 46, 1959.
26. Bowen, J. P.; Pathiaseril, A.; Proferta, S.; Allinger, N. L. J. Org. Chem., 1987, 52, 5162.
27. Kellie, G. M.; Riddell, F. G. In Topics in Stereochemistry; Eliel, E. L., Allinger, N. L. Eds., Wiley-Interscience: New York, 1974; Vol. 8, p 225.
28. Hehre, W. J.; Radom, L.; Schleyer, P. v. P.; Pople, J. A. Ab initio Molecular Orbital Theory; Wiley: New York, 1986.
29. Frisch, M. J.; Head-Gordon, M.; Trucks, G. W.; Foresman, J. B.; Schlegel, H. B.; Raghavachari, K.; Robb, M.; Binkley, J. S.; Gonzalez, C.; Defrees, D. J.; Fox, D. J.; Whiteside, R. A.; Seeger, R.; Melius, C. F.; Baker, J.; Martin, R. L.; Kahn, L. R.; Stewart, J. J. P.; Topiol, S.; Pople, J. A. Gaussian 90, revision H; Gaussian, Inc.: Pittsburgh, PA, 1990.
30. Pickett, H. M.; Strauss, H. L. J. Am. Chem. Soc. 1970, 92, 7281, and references therein.