Role of heteroatoms in diastereofacial control in cycloaddition to a dissymmetric cyclohexa-1,3-diene moiety in a polycyclic framework. Remarkable stereodirecting influence of distal protective groups

Journal of Organic Chemistry

Volumn 65, Issue 6, 2000, Pages 1685-1696

  Mehta, Goverdhan ^a,b   Uma, R ^a,b  

^a UNIVERSITY OF HYDERABAD   (India)

^b INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

HEXACYCLOPENTADECA 2,4 DIENE 7,15 DIONE; POLYCYCLIC AROMATIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BINDING; CRYSTAL STRUCTURE; MOLECULAR INTERACTION; ORGANIC CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0034708810     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991349b     Document Type: Article

References (46)

1. For a series of articles on diastereoselection, see: Thematic Issue on Diastereoselection Chem. Rev. 1999, 99(5).
2. (a) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon: Oxford, 1990.
3. (b) Fringuelli, F.; Taticchi, A. Dienes in the Diels-Alder Reaction; John Wiley and Sons: New York, 1990.
4. (a) Fallis, A. G.; Lu, Y.-F. In Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: London, 1993, Vol. 3, Chapter 1.
5. (b) Mehta, G.; Uma, R. Acc. Chem. Res., in press.
6. (a) Burnell, D. J.; Valenta, Z. J. Chem. Soc., Chem. Commun. 1985, 1247
7. (b) Brown, F. K.; Houk, K. N.; Burnell, D. J.; Valenta, Z. J. Org. Chem. 1987, 52, 3050.
8. (c) Adam, W.; Jacob, U.; Prein, M. J. Chem. Soc., Chem. Commun. 1995, 839.
9. (a) Poirier, R. A.; Pye, C. C.; Xidos, J. D.; Burnell, D. J. J. Org. Chem. 1995, 60, 2328.
10. (b) Xidos, J. D.;Poirier, R. A.; Pye, C. C.; Burnell, D. J. J. Org. Chem. 1998, 63, 105.
11. Angell, E. C.; Fringuelli, F.; Pizzo, B.; Taticchi, A.; Wenkert, E. J. Org. Chem. 1986, 51, 2642.
12. Hagenbuch, J. P.; Vogel, P.; Pinkerton, A. A.; Schwarzenbach, D. Helv. Chim. Acta 1981, 64, 1818.
13. Brown, F. K.; Houk, K. N. J. Am. Chem. Soc. 1985, 107, 1971.
14. Inagaki, S.; Fujimoto, H.; Fukui, K. J. Am. Chem. Soc. 1976, 98, 4054.
15. (a) Paquette, L. A.; Carr, R. V. C.; Bohm, M. C.; Gleiter, R. J. Am. Chem. Soc. 1980, 102, 1186.
16. (b) Gleiter, R.; Paquette, L. A. Acc. Chem. Res. 1983, 16, 328 and references therein.
17. (a) Gleiter, R.; Ginsburg, D. Pure Appt. Chem. 1979, 51, 1301.
18. (b) Ginsburg, D. Tetrahedron 1983, 39, 2095.
19. (a) Cieplak, A. S. J. Am. Chem. Soc. 1981, 103, 4540.
20. (b) Cieplak, A. S. Chem. Rev. 1999, 99, 1265.
21. (c) Coxon, J. M.; McDonald, D. Q. Tetrahedron Lett. 1992, 33, 651.
22. Kahn, S. D.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 663.
23. Anh, N. T.; Tetrahedron 1973, 29, 3227.
24. (a) Fessner, W. D.; Grund, C.; Prinzbach, H. Tetrahedron Lett. 1991, 32, 5935.
25. (b) Fessner, W. D.; Scheumann, K.; Prinzbach, H. Tetrahedron Lett. 1991, 32, 5939.
26. Mehta, G.; Padma, S.; Reddy, H. K.; Nethaji, M. J. Chem. Soc., Perkin Trans. 1 1994, 2049.
27. (a) Coxon, J. M.; O'Connell, M. J.; Steel, P. J. J. Org. Chem. 1987, 52, 4726.
28. (b) Coxon, J. M.; Maclagan, R. G. A. R.; McDonald, D. Q.; Steel, P. J. ibid. 1991, 56, 2542.
29. (c) Coxon, J. M.; Fong, S. T.; McDonald, D. Q.; Steel, P. J. Tetrahedron Lett. 1993, 34, 163.
30. (d) Coxon, J. M.; O'Connell, M. J.; Steel, P. J. Acta Crystallogr. 1986, C42, 1773.
31. (a) Pandey, B.; Zope, U. R.; Ayyangar, N. R. Synth. Commun. 1989, 19, 585.
32. (b) Dhaneshwar, N. N.; Tavale, S. S.; Guru Row: T. N.; Zope, U. R.; Pandey, B.; Ayyanger, N. R. Acta Crystallogr. 1988, C44, 2191.
33. (a) Fillipesen, N.; Menter, J. M. J. Chem. Soc., B 1969, 616.
34. (b) Kushner, A. S. Tetrahedron Lett. 1971, 12, 3275.
35. (c) Mehta, G.; Singh, V.; Rao, K. S. Tetrahedron Lett. 1980, 21, 1369.
36. Macaulay, J. B.; Fallis, A. G. J. Am. Chem. Soc. 1990, 112, 1136.
37. Paquette, L. A.; Branan, B. M.; Rogers, R. D.; Bond, A. H.; Lange, H.; Gleiter, R. J. Am. Chem. Soc. 1995, 117, 5992 and references therein.
38. Mehta, G.; Uma, R.; Pramanik, A.; Chandrasekhar, J.; Nethaji, M. J. Chem. Soc., Chem. Commun. 1995, 677.
39. A portion of this work dealing with the cycloadditions to acetals has been published as a preliminary communication, see: Mehta, G.; Uma, R. Tetrahedron Lett. 1995, 36, 4873.
40. Bohm, M.; Gleiter, R. Tetrahedron 1980, 36, 3209.
41. 28
42. Dox, A. W. Organic Synthesis; Wiley: New York, 1941; Collect. Vol. 1, p 266.
43. Fieser, L. F.; Fieser, M. Reagents for Organic Synthesis; John-Wiley: New York, 1967; p 737.
44. Mehta, G.; Uma, R. Tetrahedron Lett. 1996, 37, 1897.
45. (a) Sheldrick, G. M. SHELX 86 program for the solution of crystal structures; University of Göttingen, Germany, 1986.
46. (b) Sheldrick, G. M. SHELX76, program for crystal structure determination, University of Cambridge, England, 1976.