Stereoselective cyclopropanation of unsaturated acetals, using carbohydrates with d-gluco, l-rhamno and d-xylo configurations as chiral auxiliaries

Tetrahedron Asymmetry

Volumn 19, Issue 14, 2008, Pages 1720-1729

  Vega Pérez, José M ^a   Periñán, Ignacio ^a   Vega, Margarita ^a   Iglesias Guerra, Fernando ^a  

^a UNIVERSITY OF SEVILLE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 O ISOPROPYLIDENE DEXTRO GLUCOFURANOSE; 1,2 O ISOPROPYLIDENE DEXTRO XYLOFURANOSE; ACETAL DERIVATIVE; CARBOHYDRATE; CARBOHYDRATE DERIVATIVE; CYCLOPROPANE; DODECYL N ACETYL 2 AMINO 2 DEOXY DEXTRO GLUCOPYRANOSIDE; HYDROXYL GROUP; METHYL DEXTRO GLUCOPYRANOSIDE; METHYL LEVO RHAMNOPYRANOSIDE;

ARTICLE; CYCLOPROPANATION; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 48349131340     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.06.018     Document Type: Article

References (46)

1. Wong H.N.C., Hon M.-Y., Tse C.-W., Yip T.-C., Tanko J., and Hudlicky T. Chem. Rev. 89 (1989) 165-198
2. Salaün J. Chem. Rev. 89 (1989) 1247-1270
3. Cativiela C., and Díaz-de-Villegas M.D. Tetrahedron: Asymmetry 11 (2000) 645-732
4. Salaün J. Top. Curr. Chem. 207 (2000) 1-67
5. Donaldson W. Tetrahedron 57 (2001) 8589-8627
6. Borger D.L., Boyce C.W., Garbaccio R.M., and Goldberg J.A. Chem. Rev. 97 (1997) 787-828
7. Kuramochi K., Matsui R., Matsubara Y., Nakai J., Sunoki T., Arai S., Nagata S., Nagahara Y., Mizushina Y., Ikekita M., and Kobayashi S. Bioorg. Med. Chem. 14 (2006) 2151-2161
8. Kim A., and Hong J.H. Eur. J. Med. Chem. 42 (2007) 487-493
9. Zhang A., Li F., Ding C., Yao Q., Knappi B.I., Bidlack J.M., and Neumeyer J.L. J. Med. Chem. 50 (2007) 2747-2751
10. Bender D.M., Peterson J.A., McCarthy J.R., Gunaydin H., Takano Y., and Houk K.N. Org. Lett. 10 (2008) 509-511
11. Lebel H., Marcoux J.-F., Molinaro C., and Charette A.B. Chem. Rev. 103 (2003) 977-1050
12. Davies H.M.L. Tetrahedron 49 (1993) 5203-5223
13. Corsaro A., Pistarà V., Catelani G., D'Andrea F., Adamo R., and Chiacchio M.A. Tetrahedron Lett. 47 (2006) 6591-6594
14. Mash E.A., and Nelson K.A. Tetrahedron 43 (1987) 679-692
15. Vallgarda J., and Hacksell U. Tetrahedron Lett. 32 (1991) 5625-5628
16. Dubs M., Dieks H., Günther W., Kötteritzsch M., Poppitz W., and Schönecker B. Tetrahedron Lett. 43 (2002) 2499-2503
17. Balsells J., and Walsh P.J. J. Org. Chem. 65 (2000) 5005-5008
18. Charette A.B., Janes M.K., and Lebel H. Tetrahedron: Asymmetry 14 (2003) 867-872
19. Long J., Du H., Li K., and Shi Y. Tetrahedron Lett. 46 (2005) 2737-2740
20. Du H., Long J., and Shi Y. Org. Lett. (2006) 2827-2829
21. Hollingsworth R.I., and Wang G. Chem. Rev. 100 (2000) 4267-4282
22. Kunz H., and Rück K. Angew. Chem., Int. Ed. Engl. 32 (1993) 336-358
23. Adam W., and Zhang A. Synlett (2005) 1047-1072
24. Pleuss N., Zech G., Furman B., and Kunz H. In: Levy D.E., and Fügedi P. (Eds). Sugars as Chiral Auxiliaries. The Organic Chemistry of Sugars (2006), Taylor & Francis Group, Boca Raton 427-488
25. Charette A.B., Côté B., and Marcoux J.-F. J. Am. Chem. Soc. 113 (1991) 8166-8167
26. Charette A.B., and Côté B. J. Org. Chem. 58 (1993) 933-936
27. Charette A.B., Turcotte N., and Marcoux J.-F. Tetrahedron Lett. 35 (1994) 513-516
28. Ferreira V.F., Leao R.A.C., Silva F.C., Pinheiro S., Lhoste P., and Sinou D. Tetrahedron: Asymmetry 18 (2007) 1217-1223
29. Kang J., Lim G.J., Yoon S.K., and Kim M.Y. J. Org. Chem. 60 (1995) 564-577
30. Iglesias-Guerra F., Romero I., Alcudia F., and Vega-Pérez J.M. Carbohydr. Res. 308 (1998) 57-62
31. Iglesias-Guerra F., Candela J.I., Bautista J., Alcudia F., and Vega-Pérez J.M. Carbohydr. Res. 316 (1999) 71-84
32. Iglesias-Guerra F., Candela J.I., Blanco E., Alcudia F., and Vega-Pérez J.M. Chirality 14 (2002) 199-203
33. Vega-Pérez J.M., Candela J.I., Blanco E., and Iglesias-Guerra F. Tetrahedron 55 (1999) 9641-9650
34. Vega-Pérez J.M., Candela J.I., and Iglesias-Guerra F. J. Org. Chem. 62 (1997) 6608-6611
35. Vega-Pérez J.M., Vega M., Blanco E., and Iglesias-Guerra F. Tetrahedron: Asymmetry 12 (2001) 135-147
36. Vega-Pérez J.M., Candela J.I., Romero I., Blanco E., and Iglesias-Guerra F. Eur. J. Org. Chem. (2000) 3949-3956
37. Vega-Pérez J.M., Candela J.I., Blanco E., and Iglesias-Guerra F. Tetrahedron: Asymmetry 13 (2002) 2471-2483
38. Vega-Pérez J.M., Vega M., Blanco E., and Iglesias-Guerra F. Tetrahedron: Asymmetry 12 (2001) 3189-3203
39. Vega-Pérez J.M., Vega M., Blanco E., and Iglesias-Guerra F. Tetrahedron: Asymmetry 15 (2004) 3617-3633
40. Vega-Pérez J.M., Vega M., Blanco E., and Iglesias-Guerra F. Tetrahedron: Asymmetry 18 (2007) 1850-1867
41. Padwa A., Blacklock T., and Tremper A. Org. Synth. 6 (1988) 893-896
42. Murphy P.V., O'Brien J.L., Gorey-Feret L.J., and Smith A.B. Tetrahedron 59 (2003) 2259-2271
43. Evans D.A., Woerpel K.A., Hinman M.M., and Faul M.M. J. Am. Chem. Soc. 113 (1991) 726-728
44. Lacasse M.C., Poulard C., and Charette A.B. J. Am. Chem. Soc. 127 (2005) 12440-12441
45. Denmark S.E., and O'Connor S.P. J. Org. Chem. 62 (1997) 584-594
46. Nishii Y., Wakimura K., Tsuchiya T., Nakamura S., and Tanabe Y. J. Chem. Soc., Perkin Trans. 1 (1996) 1243-1249