C2-chiral substituted cis-1,3,5,7-tetraazadecalins as proton sponges: A computational study

European Journal of Organic Chemistry

Volumn , Issue 21, 2006, Pages 4938-4942

  Singh, Ajeet ^a   Chakraborty, Shampa ^a   Ganguly, Bishwajit ^a  

^a CSIR CENTRAL SALT AND MARINE CHEMICALS RESEARCH INSTITUTE   (India)

Author keywords

Chiral ligands; DFT calculations; Proton sponge; Protonation; Substituted azadecalins

Indexed keywords

EID: 33750892423     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600445     Document Type: Article

References (31)

1. a) H. A. Staab, T. Saupe, Angew. Chem. Int. Ed. Engl. 1988, 27, 865-879;
2. b) C. Krieger, I. Newson, M. A. Zirnstein, H. A. Staab, Angew. Chem. Int. Ed. Engl. 1989, 28, 84-86;
3. c) M. A. Zirnstein, H. A. Staab, Angew. Chem. Int. Ed. Engl. 1987, 26, 460-461;
4. d) H. A. Staab, K. K. Elbl-Weier, C. Krieger, Eur. J. Org. Chem. 2000, 327-333;
5. e) H. A. Staab, A. Kirsch, T. Barth, C. Krieger, F. A. Neugebauer, Eur. J. Org. Chem. 2000, 1617-1622.
6. R. W. Alder, Chem. Rev. 1989, 89, 1215-1223.
7. T. Isobe, K. Fukuda, T. Ishikawa, J. Org. Chem. 2000, 65, 7770-7773.
8. H. A. Staab, A. Kirsch, T. Barth, C. Krieger, F. A. Neugebauer, Eur. J. Org. Chem. 2000, 8, 1617-1622.
9. P. Hodgson, G. C. Lloyd-Jones, M. Murray, T. M. Peakman, R. L. Woodward, Chem. Eur. J. 2000, 6, 4451-4460.
10. a) R. W. Alder, J. Am. Chem. Soc. 2005, 127, 7924-7935;
11. b) M. C. Elliott, E. Williams, S. T. Howard, J. Chem. Soc., Perkin Trans. 2 2002, 2, 201-203.
12. A. G. Santos, W. Klute, J. Torode, V. P. W. Bohm, E. Cabrite, J. Runsink, R. W. Hoffmann, New J. Chem. 1998, 22, 993-997.
13. a) B. Ganguly, D. A. Freed, M. C. Kozlowski, J. Org. Chem. 2001, 66, 1103-1108;
14. b) Z. Xu, M. C. Kozlowski, J. Org. Chem. 2002, 67, 3072-3078.
15. O. Reany, I. Goldberg, S. Abramson, L. Golender, B. Ganguly, B. Fuchs, J. Org. Chem. 1998, 63, 8850-8859.
16. a) A. Gobbi, G. Frenking, J. Am. Chem. Soc. 1993, 115, 2362-2372;
17. b) R. Notario, J. Elguero, J. Chem. Soc., Chem. Commun. 1995, 154;
18. c) M. Peräkylä, J. Org. Chem. 1996, 61, 7420-7425;
19. d) E. Fujiwara, K. Omoto, H. Fujimoto, J. Org. Chem. 1997, 62, 7234-7238;
20. e) S. T. Howard, J. Am. Chem. Soc. 2000, 122, 8238-8244;
21. f) Z. B. Maksić, B. Kovacevic, J. Org. Chem. 2000, 65, 3303-3309;
22. g) V. Raab, K. Harms, J. Sundermeyer, B. Kovačević, Z. B. Maksić, J. Org. Chem. 2003, 68, 8790-8797;
23. h) V. Raab, E. Gauchenova, A. Merikoulov, K. Harms, J. Sundermeyer, B. Kovačević, Z. B. Maksić, J. Am. Chem. Soc. 2005, 127, 15738-15743;
24. i) M. Alcami, O. Mó, M. Yañez, J. Phys. Org. Chem. 2002, 15, 174;
25. j) M. Alcami, O. Mó, M. Yañez, Mass Spectrom. Rev. 2001, 20, 195-245.
26. Y. K. Lau, P. P. S. Saluja, P. Kebarle, R. W. Alder, J. Am. Chem. Soc. 1978, 100, 7328-7333.
27. a) R. Yamdagni, P. Kebarle, J. Am. Chem. Soc. 1973, 95, 3504-3510.
28. a) Jaguar, ed. 5.5, Schrodinger, Inc., Portland, Oregon, 2004;
29. b) A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652;
30. c) C. T. Lee, W. T. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
31. S. F. Boys, F. Bernardi, Mol. Phys. 1970, 19, 553.