1,3-Dipolar cycloadditions of D-erythrose- and D-threose-derived alkenes with nitrones

Collection of Czechoslovak Chemical Communications

Volumn 68, Issue 5, 2003, Pages 951-964

  Blanáriková Hlobilová, Iva ^a   Fišera, Lubor ^a   Prónayová, Nad'A ^a   Koman, Marian ^a  

^a SLOVAK UNIVERSITY OF TECHNOLOGY   (Slovakia)

Author keywords

Carbohydrates; Chiral alkenes; Chiral nitrones; Dipolar cycloadditions; Isoxazolidines; Polyols; Stereoselectivity; Wittig reaction

Indexed keywords

1,2 DIDEOXY 3,5 O ETHYLIDENE DEXTRO ERYTHRO PENT 1 ENITOL; 2 BENZYL 3 (5 HYDROXY 2 METHYL 1,3 DIOXAN 4 YL) 5 (5 HYDROXY 2 METHYL 1,3 DIOXAN 4 YL)ISOXAZOLIDINE; 2 BENZYL 5 [5 [(TERT BUTYLDIMETHYLSILYL)OXY] 2 METHYL 1,3 DIOXAN 4 YL] 3 (5 HYDROXY 2 METHYL 1,3 DIOXAN 4 YL)ISOXAZOLIDINE; 4 (O TERT BUTYLDIMETHYLSILYL) 1,2 DIDEOXY 3,5 O ETHYLIDENE DEXTRO ERYTHRO PENT 1 ENITOL; 4 (O TERT BUTYLDIMETHYLSILYL) 1,2 DIDEOXY 3,5 O ETHYLIDENE DEXTRO THREO PENT 1 ENITOL; 4 (O TERT BUTYLDIPHENYLSILYL) 1,2 DIDEOXY 3,5 O ETHYLIDENE DEXTRO ERYTHRO PENT 1 ENITOL; 4 (O TERT BUTYLDIPHENYLSILYL) 1,2 DIDEOXY 3,5 O ETHYLIDENE DEXTRO ETHYLIDENE DEXTRO THREO PENT 1 ENITOL; ALKENE; NITRONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CYCLOADDITION; INFRARED SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; THIN LAYER CHROMATOGRAPHY;

EID: 0038044635     PISSN: 00100765     EISSN: None     Source Type: Journal    
DOI: 10.1135/cccc20030951     Document Type: Article

References (20)

1. a) Tufariello J. J. in: 1,3-Dipolar Cycloaddition Chemistry (A. Padwa, Ed.), Chap. 9, p. 83. Wiley-Interscience, New York 1984;
2. b) Torssell K. B. G.: Nitrile Oxides, Nitrones, and Nitronates. VCH Publishers, New York 1988;
3. c) Gothelf K. V., Jorgensen K. V.: Chem. Rev. (Washington, D. C.) 1988, 98, 863.
4. Fišera L., Al-Timari U. A. R., Ertl P.: Cycloadditions in Carbohydrate Chemistry, p. 158. ACS Monograph. Am. Chem. Soc., Washington 1992.
5. Frederickson M.: Tetrahedron 1997, 53, 403.
6. a) Al-Timari U. A. R., Fišera L., Ertl P., Goljer I., Prónayová N.: Monatsh. Chem. 1992, 123, 999;
7. b) Kubán J., Blanáriková I., Fišera L., Prónayová N.: Chem. Pap. 1997, 51, 378.
8. a) Denmark S. E., Hurd R. A., Sacha H. J.: J. Org. Chem. 1997, 62, 1668;
9. b) McGaig A. E., Meldrum K. P., Wightman R. H.: Tetrahedron 1998, 54, 9429;
10. c) Hall A., Meldrum K. P., Therond P. R., Wightman R. H.: Synlett 1997, 123;
11. d) Müller R., Leibold T., Pätzel M., Jäger V.: Angew. Chem., Int. Ed. Engl. 1994, 33, 1295.
12. Taylor D. L., Nash R., Fellows L. E., Kang M. S., Syms A. S.: Antivir. Chem. Chemother. 1992, 3, 273.
13. a) Kubán J., Blanáriková I., Fišera L., Jarošková L., Fengler-Veith M., Jäger V., Kozíšek J., Humpa O., Langer V.: Tetrahedron 1999, 55, 9501;
14. b) Kubán J., Kolarovič A., Fišera L., Jäger V., Humpa O., Prónayová N., Ertl P.: Synlett 2001, 1862;
15. c) Kubán J., Kolarovič A., Fišera L., Jäger V., Humpa O., Prónayová N.: Synlett 2001, 1866;
16. d) Fischer R., Drucková A., Fišera L., Rybár A., Hametner C., Cyranski M. K.: Synlett 2002, 1113.
17. a) Barker R., MacDonald D. L.: J. Am. Chem. Soc. 1960, 82, 2301;
18. b) Ball D. H.: J. Org. Chem. 1966, 31, 220.
19. Wróblewski A. E: Z. Naturforsch., B: Chem. Sci. 1985, 40, 407.
20. Kampf A., Felstien A., Dimant E.: Carbohydr. Res. 1968, 6, 220.