Effect of the heteroatomic substituent on the pi-facial diastereoselectivity in Lewis acid catalyzed carbonyl ene reaction: A theoretical study

Journal of Molecular Structure: THEOCHEM

Volumn 858, Issue 1-3, 2008, Pages 107-112

  Chakrabarty, Kuheli ^a   Roy, Sukhendu ^a   Das, Gourab Kanti ^a  

^a VISVA BHARATI UNIVERSITY   (India)

Author keywords

Diastereoselectivity; Ene reaction; Transition structures

Indexed keywords

EID: 43049101972     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2008.02.029     Document Type: Article

References (27)

1. Hoffmann R.W. Angew. Chem. Int. Ed. Engl. 23 (1984) 932
2. Yamamoto Y. Acc. Chem. Res. 20 (1987) 243
3. Hoffmann R.W. Int. Ed. Engl. 26 (1987) 489
4. Mikami K., Loh T.P., and Nakai T. Tetrahedron Asymmetry 1 (1990) 13
5. Mikami K., Kaneko M., Loh T.P., Terada M., and Nakai T. Tetrahedron Lett. 31 (1990) 3909
6. Cram D.J., and Elhafez F.A.A. J. Am. Chem. Soc. 74 (1952) 5821
7. Cram D.J., and Kopeckycky K.R. J. Am. Chem. Soc. 81 (1959) 2748
8. Cherest M., Felkin H., and Prudent N. Tetrahedron Lett. (1968) 2205
9. Anh N.T., and Eisenstein O. Tetrahedron Lett. (1976) 155
10. Huet J., Bernard Y.M., Anh N.T., and Seyden-Penne J. Tetrahedron Lett. (1976) 159
11. Anh N.T., and Eisenstein O. Nouv. J. Chem. 1 (1977) 61
12. Anh N.T. Top. Curr. Chem. 88 (1980) 145
13. Cieplak A.S. J. Am. Chem. Soc. 103 (1981) 4540
14. Paddon-Row M.N., Wu Y.D., and Houk K.N. J. Am. Chem. Soc. 114 (1992) 10638
15. Ganguly B., Chandrasekhar J., Khan F.A., and Mehta G. J. Org. Chem. 58 (1993) 1734
16. Mehta G., and Chandrasekhar J. Chem. Rev. 99 (1999) 1437
17. Chakrabarty K., Roy S., Das G.K., and Mondal N. J. Mol. Struct. (Theochem) 805 (2007) 1-7
18. Mikami K., and Shimizu M. Chem. Rev. 92 (1992) 1021
19. Mondal N., Chakrabarty K., Roy S., and Das G.K. J. Mol. Struct. (Theochem) 684 (2004) 187-195
20. Mondal N., Mandal S.C., and Das G.K. J. Mol. Struct. (Theochem) 680 (2004) 73-81
21. Pranata J. Int. J. Quant. Chem. 62 (1997) 502
22. Schaftennar G., and Noordik J.H. J. Comput. Aid. Mol. Des. 14 (2000) 123
23. Schmidt M.W., Baldridge K.K., Boatz J.A., Elbert S.T., Gordon M.S., Jensen J.J., Koseki S., Matsunaga N., Nguyen K.A., Su S., Windus T.L., Dupuis M., and Montgomery J.A. J. Comput. Chem. 14 (1993) 13
24. Gadre S.R., and Shirsat R.N. Electrostatics of Atoms and Molecules (2000), Universities Press (India) Limited Chapter 2
25. Loncharich R.J., and Houk K.N. J. Am. Chem. Soc. 109 (1987) 6947-6952
26. Inagaki S., Fujimoto H., and Fukui K. J. Am. Chem. Soc. 98 (1976) 4693-4701
27. Salomon M.F., Pardo S.N., and Salomon R.G. J. Am. Chem. Soc. 102 (1980) 2473