Highly regioselective ring opening of oxiranes with phenoxides in the presence of β-cyclodextrin in water

Journal of Organic Chemistry

Volumn 68, Issue 12, 2003, Pages 4994-4995

  Surendra, K ^a   Krishnaveni, N Srilakshmi ^a   Nageswar, Y V D ^a   Rao, K Rama ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

REGIOSELECTIVITY;

CATALYSTS; ORGANIC SOLVENTS; WATER;

ETHERS;

ACETONE; BETA CYCLODEXTRIN; CYCLODEXTRIN; EPOXIDE; ETHYLENE OXIDE; HEXANE; SOLVENT; WATER;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; STEREOCHEMISTRY; X RAY POWDER DIFFRACTION;

CATALYSIS; CYCLIZATION; CYCLODEXTRINS; ETHERS; ETHYLENE OXIDE; MOLECULAR STRUCTURE; SOLVENTS; STEREOISOMERISM; WATER;

EID: 0037940082     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034194n     Document Type: Article

References (34)

1. (a) Wright, J. L.; Gregory, T. F.; Heffner, T. G.; MacKenie, R. G.; Pugsley, T. A.; Meulen, S. V.; Wise, L. D. Bioorg. Med. Chem. Lett. 1997, 1377.
2. (b) Baker, N. R.; Byrne, N. R.; Byrne, N. G.; Economide, A. P.; Javeld, T. Chem. Pharm. Bull. 1995, 1045.
3. (c) Kirkup, M. P.; Rizvi, R.; Shankar, B. B.; Duggar, S.; Clader, J.; McCombie, S. W.; Lin, S.; Yumibe, N.; Huie, K.; Heek, M.; Compton, D. S.; Davis, H. R.; McPhail, A. T. Bioorg. Med. Chem. Lett. 1996, 2069.
4. (a) Parker, R. E.; Isaacs, N. S. Chem. Rev. 1959, 59, 737.
5. (b) Bonini, C.; Righi, G. Synthesis 1994, 225.
6. (c) Paknikar, S. K.; Kirtane, J. G. Tetrahedran 1983, 39, 2323.
7. (d) Smith, J. G. Synthesis 1984, 629.
8. (a) Fulop, F.; Huber, I.; Bernath, G.; Honing, H.; Seyferwesserthal, P. Synthesis 1991, 43.
9. (b) Iranpoor, N.; Shekarriz, M. Synth. Commun. 1999, 29, 2249.
10. (c) Ciaccio, J. A.; Stanescu, C.; Bontemps, J. Tetrahedron Lett. 1992, 33, 1431.
11. (d) Chini, M.; Crotti, P.; Favero, L.; Macchia, F. Tetrahedron Lett. 1991, 32, 4775.
12. (e) Chini, M.; Crotti, P.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lett. 1994, 35, 433.
13. Scriveni, E. F. V.; Turnbull, K. Chem. Rev. 1988, 88.
14. (a) Iranpoor, N.; Salehi, P. Tetrahedron 1995, 51, 909.
15. (b) Iranpoor, N.; Zeynizadeh, B. Synthesis 1999, 29, 1071.
16. (c) Iranpoor, N.; Tarrian, T.; Movahedi, Z. Synthesis 1996, 1473.
17. (a) Bonini, C.; Righi, G. Synthesis 1994, 225.
18. (b) Reference 11a and references therein.
19. Reddy, L. R.; Reddy, M. A.; Bhanumathi, N.; Rao, K. R. New J. Chem. 2001, 25, 221 and references therein.
20. Yadav, J. S.; Reddy, B. V. S.; Gakul, B. Chem. Lett. 2002, 906.
21. Chem, J.; Shum, W. Tetrahedron Lett. 1995, 36, 2379.
22. Iranpoor, N.; Firouzabadi, H.; Safavi, A.; Shekarriz, M. Synth. Commun. 2002, 32, 2287.
23. (a) Reddy, M. A.; Surendra, K.; Bhanumathi, N.; Rao, K. R. Tetrahedron 2002, 58, 6003.
24. (b) Reddy, M. A.; Bhanumathi, N.; Rao, K. R. Tetrahedron Lett. 2002, 43, 3237.
25. (c) Reddy, M. A.; Bhanumathi, N.; Rao, K. R. Chem. Commun. 2001, 1974.
26. (d) Reddy, L. R.; Bhanumathi, N.; Rao, K. R. Chem. Commun. 2000, 2321.
27. (e) Reddy, L. R.; Reddy, M. A.; Bhanumathi, N.; Rao, K. R. Synlett 2000, 339.
28. (f) Reddy, M. A.; Reddy, L. R.; Bhanumathi, N.; Rao, K. R. New J. Chem. 2001, 25, 359.
29. (g) Reddy, M. A.; Reddy, L. R.; Bhanumathi, N.; Rao, K. R. Chem. Lett. 2001, 246.
30. Shigeki, M.; Das, J.; Roels, J.; Vogl, E. M.; Yamamoto, N.; Iida, T.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 2252.
31. Szejtli, J.; Osa, T. Comprehensive Supramolecular Chemistry; Pergamon: Oxford, U.K. 1996; Vol. 3, p 253.
32. Demarco, P. V.; Thakkar, A. L. Chem. Commun. 1970, 2.
33. (a) Stephenson, O. J. Chem. Soc. 1954, 1571.
34. (b) Kornblum, N.; Lurie, A. P. J. Am. Chem. Soc. 1959, 81, 2705.