Evidence for cyclodextrin dioxiranes. Part 2. Catalytic and enantioselective properties of cyclodextrin dioxiranes formed from keto-derivatised hydroxypropyl-cyclodextrins

Carbohydrate Research

Volumn 317, Issue 1-4, 1999, Pages 10-18

  Deary, Michael E ^a   Davies, D Martin ^a  

^a NORTHUMBRIA UNIVERSITY   (United Kingdom)

Author keywords

Bromine oxidation; Cyclodextrin; Dioxirane; Hydroxypropyl cyclodextrin; Ketone

Indexed keywords

2 HYDROXYPROPYL BETA CYCLODEXTRIN; ALPHA CYCLODEXTRIN; BETA CYCLODEXTRIN; CYCLODEXTRIN DERIVATIVE; KETONE; SUCROSE;

ARTICLE; CARBOHYDRATE SYNTHESIS; CHEMICAL REACTION; ENANTIOMER; KINETICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PRIORITY JOURNAL;

EID: 0032777105     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(99)00061-0     Document Type: Article

References (26)

1. Deary M.E., Davies D.M. Carbohydr. Res. 309:1998;17.
2. For a recent review see: R.W. Breslow, S.D. Dong, Chem. Rev., 98 (1998) 1997 and references therein.
3. D.M. Davies, M.E. Deary, J. Chem. Soc., Perkin Trans. 2, (1999) 1027.
4. VanEtten R.L., Sebastian J.F., Clowes G.A., Bender M.L. J. Am. Chem. Soc. 89:1967;3242.
5. Tee O.S., Mazza C., Du X. J. Org. Chem. 55:1990;3603.
6. K.R. Rao, T.N. Srinivasan, N. Bhanumathi, P.B. Sattur, J. Chem. Soc., Chem. Commun., (1990) 10.
7. Cramer F., Mackensen G. Angew. Chem., Int. Ed. Engl. 5:1966;601.
8. Martin K.A., Mortellaro M.A., Sweger R.W., Fikes L.E., Winn D.T., Clary S., Johnson M.P., Czarnik A.W. J. Am. Chem. Soc. 117:1995;10443.
9. For reviews of dioxirane chemistry see: (a) W.A. Adam, R. Curci, J.O. Edwards, Acc. Chem. Res., 22 (1989) 205. (b) R.W. Murray, Chem. Rev. 89 (1989) 1187.
10. For reviews of dioxirane chemistry see: (a) W.A. Adam, R. Curci, J.O. Edwards, Acc. Chem. Res., 22 (1989) 205. (b) R.W. Murray, Chem. Rev. 89 (1989) 1187.
11. Larm O., Larsson K., Scholander E., Meyer B., Thiem J. Carbohydr. Res. 91:1981;13.
12. Mortellaro M.A., Hong S., Winn D.T., Czarnik A.W. Bioorg. Med. Chem. Lett. 4:1994;2041.
13. Xu H., Wentworth P.J., Howell N.W., Joens J.A. Spectrochim. Acta. 49:1993;1171.
14. Edwards J.O., Pater R.H., Curci R., Di Furia F. Photochem. Photobiol. 30:1979;63.
15. D.M. Davies, M.E. Deary, J. Chem. Soc., Perkin Trans. 2, (1995) 1287.
16. Cramer F., Dietsche W. Chem. Ber. 92:1959;378.
17. Hinze W.L., Rieh T.E., Armstrong D.W., DeMond W., Alak A., Ward T. Anal. Chem. 57:1985;237.
18. (a) M. Mikolajczyk, J. Drabowicz, J. Am. Chem. Soc., 100 (1978) 2510.
19. (b) M. Mikolajczyk, J. Drabowicz, F. Cramer, J. Chem. Soc., Chem. Commun., (1971) 317.
20. A. Czarnik, J. Org. Chem., 49 (1984) 924. See also: R. Fornasier, P. Scrimin, P. Tecilla, U. Tonellato, Phosphorus Sulfur, 35 (1988) 211.
21. A. Czarnik, J. Org. Chem., 49 (1984) 924. See also: R. Fornasier, P. Scrimin, P. Tecilla, U. Tonellato, Phosphorus Sulfur, 35 (1988) 211.
22. Gallopo A.R., Edwards J.O. J. Org. Chem. 46:1981;1684.
23. Ibene-Rasa K.M., Edwards J.O. J. Am. Chem. Soc. 84:1962;763.
24. V.M. Paradkar, T.B. Latham, D.M. Demko, Synlett, (1995) 1059.
25. (a) For 4-bromopyridine N-oxide: J.P. Phillips, H. Feuer, B.S. Thyagarajan (Eds.), Organic Electronic Spectral Data, Vol. 8, Interscience, New York, 1966.
26. (b) For pryridine N-oxide: (Eds.), Organic Electronic Spectral Data, Vol. 15, Interscience, New York, 1973.