Quasienantiomeric levoglucosenone and isolevoglucosenone allow the parallel kinetic resolution of a racemic nitrone

Journal of Organic Chemistry

Volumn 73, Issue 5, 2008, Pages 1999-2002

  Cardona, Francesca ^a   Lalli, Daniela ^a   Faggi, Cristina ^a   Goti, Andrea ^a   Brandi, Alberto ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

PARALLEL KINETIC RESOLUTION; RACEMIC NITRONE;

CHIRALITY; CYCLOADDITION; ENANTIOMERS; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

NITROGEN OXIDES;

DISACCHARIDE; ISOLEVOGLUCOSENONE; LEVOGLUCOSENONE; NITRONE; OXIDE; PYRROLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIRALITY; CYCLOADDITION; ENANTIOMER; KINETICS; STEREOCHEMISTRY; SYNTHESIS;

BICYCLO COMPOUNDS, HETEROCYCLIC; GLUCOSE; KINETICS; NITROGEN OXIDES; STEREOISOMERISM;

EID: 41149177725     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702403b     Document Type: Article

References (31)

1. (a) Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1997, 119, 2584-2585.
2. (b) Eames, J. Angew. Chem., Int. Ed. 2000, 39, 885-888.
3. (c) Zhang, Q.; Curran, D. P. Chem. Eur. J. 2005, 11, 4866-4880.
4. For some recent PKRs see: (a) Tanaka, K.; Hagiwara, Y.; Hirano, M. Angew. Chem., Int. Ed. 2006, 45, 2734-2737.
5. (b) Vedejs, E.; Rozners, E. Angew. Chem., Int. Ed. 2001, 123, 2428-2429.
6. (c) Chavda, S.; Coulbeck, E.; Coumbarides, G. S.; Dingjan, M.; Eames, J.; Ghilagaber, S.; Yohannes, Y. Tetrahedron: Asymmetry 2006, 17, 3386-3399.
7. For a review, see: Cardona, F.; Goti, A.; Brandi, A. Eur. J. Org. Chem. 2001, 2999-3011 and references cited therein.
8. Pietrusiewicz, K. M.; Holody, W.; Koprowski, M.; Cicchi, S.; Goti, A.; Brandi, A. Phosporus Sulfur Silicon 1999, 146, 389-392.
9. Cardona, F.; Valenza, S.; Goti, A.; Brandi, A. Eur. J. Org. Chem. 1999, 1319-1323.
10. For a recent review on chiral cyclic nitrones see: Revuelta, J.; Cicchi, S.; Goti, A.; Brandi, A. Synlett 2007, 485-504.
11. Eliel, E. L.; Wilen, S. H.; Mander, L. N. In Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994; p 1205.
12. Cardona, F.; Goti, A.; Brandi, A. Org. Lett. 2003, 5, 1475-1478.
13. Witczak, Z. J., Ed. Levoglucosenone and Levoglucosans, Chemistry and Application; ATL Press: Mount Prospect, 1994.
14. Horton, D.; Norris, P.; Roski, J. J. Org. Chem. 1996, 61, 3783-3793.
15. Awad, L.; Demange, R.; Zhu, Y.-H.; Vogel, P. Carbohydr. Res. 2006, 341, 1235-1252 and references cited therein.
16. (a) Blake, A. J.; Forsyth, A. C.; Paton, R. M. J. Chem. Soc., Chem. Commun. 1988, 440-442.
17. (b) Blake, A. J.; Cook, T. A.; Forsyth, A. C.; Gould, R. O.; Paton, R. M. Tetrahedron 1992, 48, 8053-8064.
18. Cicchi, S.; Höld, I.; Brandi. A. J. Org. Chem. 1993, 58, 5274-5275.
19. Cicchi, S.; Goti, A.; Brandi, A. J. Org. Chem. 1995, 60, 4743-4748.
20. Goti, A.; Cicchi, S.; Cacciarini, M.; Cardona, F.; Fedi, V.; Brandi, A. Eur. J. Org. Chem. 2000, 3633-3645.
21. 3 as a chiral shift reagent.
22. 1H NMR spectrum of the crude reaction mixtures.
23. Robina, I.; Vogel, P. Synthesis 2005, 675-702.
24. (a) Cardona, F.; Valenza, S.; Picasso, S.; Goti, A.; Brandi, A. J. Org. Chem. 1998, 63, 7311-7318.
25. (b) Postema, M. H. D.; Piper, J. L.; Liu, L.; Shen, J.; Faust, M.; Andreana, P. J. Org. Chem. 2003, 68, 4748-4754.
26. (c) Leeuwenburgh, M. A.; Picasso, S.; Overkleeft, H. S.; Van der Marel, G. A.; Vogel, P.; Van Boom, J. H. Eur. J. Org. Chem. 1999, 1185-1189.
27. (d) Pasquarello, C.; Demange, R.; Vogel, P. Bioorg. Med. Chem. Lett. 1999, 9, 793-796.
28. (e) Kraehenbuehl, K.; Picasso, S.; Vogel, P. Helv. Chim. Acta 1998, 81, 1439-1479.
29. (f) Marquis, C.; Picasso, S.; Vogel, P. Synthesis 1999, 1441-1452.
30. Pasquarello, C.; Picasso, S.; Demange, R.; Malissard, M.; Berger, E. G.; Vogel, P. J. Org. Chem. 2000, 65, 4251-4260.
31. Vogel, P.; Gerber-Lemaire, S.; Fiaux, H.; Popowycz, F.; Favre, S.; Juillerat-Jeanneret, L. Abstracts of Papers; 230th ACS National Meeting, Washington, DC, Aug 28-Sept 1 2005; American Chemical Society: Washington, DC, CARB-028.