Experimental determination of the activation parameters and stereoselectivities of the intramolecular Diels-Alder reactions of 1,3,8-nonatriene, 1,3,9-decatriene, and 1,3,10-undecatriene and transition state modeling with the Monte Carlo-Jumping between Wells/molecular dynamics method

Journal of the American Chemical Society

Volumn 119, Issue 43, 1997, Pages 10255-10259

  Diedrich, Matthias K ^a   Klärner, Frank Gerrit ^a   Beno, Brett R ^b   Houk, K N ^b   Senderowitz, Hanoch ^c   Still, W Clark ^c  

^a UNIVERSITY OF DUISBURG ESSEN   (Germany)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOALKENE;

ARTICLE; DRUG SYNTHESIS; ENTROPY; IN VITRO STUDY; MOLECULAR DYNAMICS; REACTION ANALYSIS; STEREOCHEMISTRY; TEMPERATURE; THEORY; THERMODYNAMICS;

EID: 0030700683     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9643331     Document Type: Article

References (36)

1. (a) Senderowitz, H.; Guarnieri, F.; Still, W. C. J. Am. Chem. Soc. 1995, 117, 8211.
2. (b) Senderowitz, H.; Parish, C.; Still, W. C. J. Am. Chem. Soc. 1996, 118, 2078.
3. (a) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16, 10.
4. (b) Oppolzer, W. Synthesis 1978, 793.
5. (c) Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41.
6. (d) Brieger, G.; Bennett, J. N. Chem. Rev. 1980, 80, 63.
7. (e) Fallis, A. G. Can. J. Chem. 1984, 62, 183.
8. (f) Ciganek, E. Org. React. 1984, 32, 1.
9. (g) Taber, D. F. Intramolecular Diels - Alder and Alder Ene Reactions; Springer-Verlag: Berlin, 1984.
10. (h) Craig, D. Chem. Soc. Rev. 1987, 16, 187.
11. Roush, W. R. In Advances in Cycloaddition; Curran, D. F., Ed.; JAI Press: Greenwich, 1990; Vol. 2, p 91.
12. (j) Okamura, W. H.; Curtin, M. L. Synlett 1990, 1, 1.
13. (k) Thomas, E. J. Acc. Chem. Res. 1991, 24, 229.
14. (l) Martin, S. F. J. Heterocyclic Chem. 1994, 31, 679.
15. (a) Raimondi, L.; Brown, F. K.; Gonzalez, J.; Houk, K. N. J. Am. Chem. Soc. 1992, 114, 4796.
16. (b) For a review of transition state modeling with empirical force fields see: Eksterowicz, J. E.; Houk, K. N. Chem. Rev. 1993, 93, 2439.
17. Lin, Y.-T.; Houk, K. N. Tetrahedron Lett. 1985, 26, 2269.
18. Brown, F. K.; Houk, K. N. Tetrahedron Lett. 1985, 26, 2297.
19. Brown, F. K.; Singh, U. C.; Kollman, P. A.; Raimondi, L.; Houk, K. N.; Bock, C. W. J. Org. Chem. 1992, 57, 4862.
20. (a) Ratoveloma, V.; Linstrumelle, G. Synth. Commun. 1981, 11, 917.
21. (b) Crombie, L.; Horsham, M. A.; Blade, R. J. Tetrahedron Lett. 1987, 28, 4879.
22. (c) Just, G.; O'Connor, B. Tetrahedron Lett. 1988, 29, 753.
23. (d) Guillerm, D.; Linstrumelle, G. Tetrahedron Lett. 1986, 27, 5857.
24. Wilke, G.; Müller, H. Chem. Ber. 1956, 89, 444.
25. Negishi, E.; Takahashi, T.; Baba, S.; van Horn, D. E.; Okukado, N. J. Am. Chem. Soc. 1987, 109, 2393.
26. (a) Mousseron, M.; Jacquier, R.; Christol, H. Bull. Soc. Chim. Fr. 1957, 346.
27. (b) Christol, H.; Jacquier, R.; Mousseron, M. Bull. Soc. Chim. Fr. 1957, 1027.
28. McKenna, J.; Norymberski, J. K.; Stubbs, R. D. J. Chem. Soc. 1959, 2502.
29. A conclusive stereochemical assignment of the two products cis-6 and trans-6 could not be achieved from the spectroscopic data and relies on the comparison of GC retention times with those of cis-4/trans-4 and cis-5/trans-5. In agreement with this assignment, the retention time of each cis bicyclic compound is larger than that of the corresponding trans isomer.
30. Goldstein, E.; Beno, B.; Houk, K. N. J. Am. Chem. Soc. 1996, 118, 6036 and references therein.
31. Allinger, N. L. J. Am. Chem. Soc. 1977, 99, 8127.
32. MacroModel V5.0: Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.
33. (a) Mitchell, M. J.; McCammon, J. A. J. Comput. Chem. 1991, 12, 271.
34. (b) Straatsma, T. P.; McCammon, J. A. J. Chem. Phys. 1989, 91, 3631.
35. (c) Straatsma, T. P.; McCammon, A. J. J. Chem. Phys. 1989, 90, 3300.
36. Guarnieri, F.; Still, W. C. J. Comput. Chem. 1994, 15, 1302.