Origin of π-facial stereoselectivity of nucleophilic addition to carbonyl compounds. Application of the exterior frontier orbital extension model to cyclohexanones with polar substituent

Tetrahedron

Volumn 55, Issue 13, 1999, Pages 3871-3882

  Tomoda, Shuji ^a   Senju, Takatoshi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CONFORMATIONAL TRANSITION; MOLECULAR INTERACTION; PRIORITY JOURNAL; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033605760     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00099-X     Document Type: Article

References (36)

1. Cieplak, A. S. J. Am. Chem. Soc. 1981, 103, 4540.
2. Gung, B. W. Tetrahedron 1996, 52, 5263.
3. Wu, Y. D.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 908.
4. (a) Chérest, M.; Felkin, H. Tetrahedron Lett. 1968, 2205.
5. (b) Chérest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199.
6. (c) Anh, N. T.; Eisenstein, O.; Lefour, J. -M.; Tran Huu Dau, M. E. J. Am. Chem. Soc. 1976, 95, 6146.
7. (d) Anh, N. T.; Eisenstein, O. Nouv. J. Chim. 1976, 1, 61.
8. (a) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev, 1988, 88, 899.
9. (b) Glendening, E. D.; Weinhold, F. "Natural Resonance Theory I. General Formalism" in Technical Report of Theoretical Chemistry Institute. 1994, No. 803.
10. Tomoda, S; Senju, T. Chem. Commun. 1999 in press.
11. Tomoda, S; Senju, T. Submitted.
12. Tomoda, S.; Senju T. Tetrahedron 1997, 53, 9057.
13. Wu, Y. -D.; Tucker, A.; Houk, K. N. J. Am. Chem. Soc. 1991, 113, 5018.
14. (a) Klopman, G. J. Am. Chem. Soc. 1968, 90, 223.
15. (b) Salem, L. ibid, 1968, 90, 543.
16. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; John Wiley & Sons: London, 1977.
17. Ohno, K.; Matsumoto, S.; Harada, Y. J. Chem. Phys. 1984, 81, 4447.
18. Bondi, A. J. Phys. Chem. 1964, 68, 441.
19. Fukui, K. Theory of Orientation and Stereoselection; Springer Verlag: Heidelberg, 1979.
20. (a) Imamura, A. Mol. Phys. 1968, 15, 225-238.
21. (b) Libit, L.; Hoffmann, R. J. Am. Chem. Soc. 1974, 96, 1370.
22. Hoffmann, R. J. Chem. Phys. 1963, 39, 1397.
23. Gaussian 94 (Revision E.2); Gaussian, Inc., Pittsburgh, PA, 1997.
24. Huzinaga, S.; Gaussian Basis Sets for Molecular Orbital Calculations; Elsevier: Amsterdam, 1984.
25. (a) Huang, X. L.; Dannenberg, J. J.; Duran, M.; Bertran, J. J. Am. Chem. Soc. 1993, 115, 4024.
26. (b) Huang, X. L.; Dannenberg, J. J. ibid, 1993, 115, 6017.
27. 8
28. (a) C. R. Johnson, B. D. Tait A. S. Cieplak, J. Am. Chem. Soc. 1987, 109, 5875.
29. (b) Cieplak, A. S.; Tait, B. D.; Johnson, C. R. J. Am. Chem. Soc. 1989, 111, 8447.
30. Amarendra, Y.; Yenkatesan, K.: Ganguly, B.: Chandrasekhar, J.; Khan, F. A.; Mehta, G. Tetrahedron Lett. 1992, 33, 3072.
31. Frenking, G.; Kohler, K. F.; Reez, M. T. Angew. Chem. Int. Ed. Engl. 1991, 30, 1146.
32. Wu, Y-D.; Houk, K. N.; Padden-Row, M. N. Angew. Chem. Internat. Ed. 1992, 31, 1019.
33. (a) Ganguly, B.; Chandrasekhar, J.; Khan, F. A.; Mehta, G.J. Org. Chem. 1993, 58, 1734.
34. (b) Mehta, G., Khan, F. A. J. Chem. Soc. Chem. Commun. 1991, 18.
35. (c) Mehta, G., Khan, F. A. J. Am. Chem. Soc. 1990, 112, 6140.
36. (d) Mehta, G., Khan, F. A.; Gadre, S. R; Shirsat, R. N.; Ganguly, B.; Chandrasekhar, J. Angew. Chem. Internat. Ed. 1994, 33, 1390.