Importance of orbital and electrostatic interactions in determining π-facial selectivities in nucleophilic additions to endo-substituted bicyclo[2.2.2]octan-2-ones

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 23, 1992, Pages 1711-1712

  Mehta, Goverdhan ^a   Khan, Faiz Ahmed ^a   Ganguly, Bishwajit ^b   Chandrasekhar, Jayaraman ^b  

^a UNIVERSITY OF HYDERABAD   (India)

^b INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049070573     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/C39920001711     Document Type: Article

References (23)

1. A. S. Cieplak, B. D. Tait and C. R. Johnson, J. Am. Chem. Soc., 1989, 111, 8447.
2. V. R. Bodepudi and W. J. ie Noble, J. Org. Chem., 1991, 56, 2001.
3. Y. D. Wu, J. A. Tucker and K. N. Houk, J. Am. Chem. Soc., 1991, 113, 5018.
4. G. Frenking, K. F. Kohler and M. T. Reetz, Angew. Chem., Int. Ed. Engl., 1991, 30, 1146.
5. L. A. Paquette, T. L. Underiner and J. C. Gallucci, J. Org. Chem., 1992, 57, 86.
6. C. K. Cheung, L. T. Tseng, M. H. Lin, S. Srivastava and W. J. le Noble, J. Am. Chem. Soc., 1986, 108, 1598.
7. C. K. Cheung, L. T. Tseng, M. H. Lin, S. Srivastava and W. J. le Noble, J. Am. Chem. Soc., 1987, 109, 7239.
8. R. L. Halterman and M. A. McEvoy, J. Am. Chem. Soc., 1990, 112, 6690.
9. G. Mehta and F. A. Khan, J. Am. Chem. Soc., 1990, 112, 6140.
10. G. Mehta and F. A. Khan, J. Chem. Soc., Chem. Commun., 1991, 18.
11. G. Mehta and M. Praveen, Tetrahedron Lett., 1992, 33, 1759.
12. H. Li, G. Mehta, S. Padma and W. J. le Noble, J. Org. Chem., 1991, 56, 2006.
13. V. Amarendra Kumar, K. Venkatesan, B. Ganguly, J. Chandrasekhar, F. A. Khan and G. Mehta, Tetrahedron Lett., 1992, 33, 3069.
14. A. S. Cieplak, J. Am. Chem. Soc., 1981, 103, 4540.
15. N. T. Anh and O. Eisenstein, Nouv. J. Chim., 1977, 1, 61.
16. S. S. Wong and M. N. Paddon-Row, J. Chem. Soc., Chem. Commun., 1990, 456.
17. B. Ganguly, J. Chandrasekhar, F. A. Khan and G. Mehta, J. Org. Chem.submitted for publication.
18. M. J. S. Dewar and W. Thiel, J. Am. Chem. Soc., 1977, 99, 4899.
19. For a discussion on the role of electrostatic interactions, see: S. S. Wong and M. N. Paddon-Row, J. Chem. Soc., Chem. Commun., 1991, 327.
20. S. S. Wong and M. N. Paddon-Row, Austr. J. Chem., 1991, 44, 765.
21. H. B. Broughton, S. M. Green and H. S. Rzepa, J. Chem. Soc., Chem. Commun., 1992, 998.
22. A. I. Meyers and R. H. Wallace, J. Org. Chem., 1989, 54, 2509.
23. E. Vedejs and W. H. Dent, J. Am. Chem. Soc., 1989, 111, 6861.