Stereospecific addition of formaldehyde dialkylhydrazones to sugar aldehydes. Synthesis of cyanohydrins and α-hydroxy aldehydes

Tetrahedron Letters

Volumn 37, Issue 32, 1996, Pages 5787-5790

  Lassaletta, José M ^a   Fernández, Rosario ^a   Martín Zamora, Eloísa ^a   Pareja, Carmen ^a  

^a UNIVERSITY OF SEVILLE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYALDEHYDE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030570887     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01226-9     Document Type: Article

References (30)

1. 1. (a) Hanessian, S. In Total Synthesis of Natural Products: The Chiron Approach, Pergamon Press, Oxford, 1983.
2. (b) Ferrier, R.J.; Middleton, S. Chem. Rev. 1993, 93, 2779-2831.
3. (c) Casiraghi, G.; Zanardi, F.; Rassu, G.; Spanu, P. Chem. Rev. 1995, 95, 1677-1716.
4. 2. (a) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A. Tetrahedron 1987, 43, 3533-3539 and references cited therein.
5. (b) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. J. Org. Chem. 1989, 54, 693-702 and references cited therein.
6. (c) Dondoni, A.; Colombo, L. Advances in the Use of Synthons in Organic Chemistry, Dondoni, A., Ed.; Jai Press LTD: Greenwich, 1993; pp. 1-49.
7. 3. (a) Lassaletta, J.-M.; Fernández, R. Tetrahedron Lett. 1992, 33, 3691-3694.
8. (b) Fernández, R.; Gasch, C.; Lassaletta, J.-M.; Llera, J.-M. Tetrahedron Lett. 1994, 55, 471-472.
9. (c) Enders, D.; Syrig, R.; Raabe, G.; Fernández, R.; Gasch, C.; Lassaletta, J.-M.; Llera, J.-M. Synthesis 1996, 48-52.
10. (c) Fernández, R.; Gasch, C.; Lassaletta, J.-M; Llera, J.-M. Synthesis 1996, 627-632.
11. (d) Lassaletta, J.-M.; Fernández, R.; Gasch, C.; Vázquez, J. Tetrahedron 1996, in press.
12. 4. (a) Vázquez, J. Reacciones de Adición de Michael de la Dimetilhidrazona del Formaldehído. Un Nuevo Equivalente del Anión Formilo, University of Seville, 1995.
13. (b) Lassaletta, J.-M.; Fernández, R.; Martín-Zamora, M.-E.; Díez, E. J. Am. Chem. Soc. 1996, in press.
14. 5. (a) North, M. Synlett 1993, 807-820.
15. (b) Effenberger, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 1555-1564.
16. 6. Danishefsky, S.J.; DeNinno, M.P. Angew. Chem., Int. Ed. Engl. 1987, 26, 15-23.
17. 1H NMR control). The solvent was removed under reduced pressure and the residue was purified by flash chromatography to afford pure 8.
18. 8. Gautier, A.; Renault, J.; Fauran, C. Bull. Soc. Chim. Fr. 1963, 2738-2741.
19. 13C NMR, IR, and high resolution mass spectroscopy and/or combustion analysis.
20. 10. Cook, A.G. In Enamines. Synthesis, Structure, and Reactions, A.G. Cook Ed.: New York, 1988; pp. 1-101.
21. 11. The inversion of the stereochemistry at the hydroxymethylene center adjacent to the hydrazone moiety, following well established literature procedures, should allow to obtain the syn isomers: Dondoni, A.; Orduna, J.; Merino, P. Synthesis 1992, 201-210 and references cited therein.
22. 12. (a) Enders, D.; Schubert, H.; Nübling, C. Angew. Chem., Int. Ed. Engl. 1986, 25, 1109-1110.
23. (b) Denmark, S.E.; Weber, T.; Piotrowski, D.W. J. Am. Chem. Soc. 1987, 109, 2224-2225.
24. (c) Weber, T.; Edwards, J.P.; Denmark, S.E. Synlett 1989, 20-22.
25. (d) Alexakis, A.; Lensen, N.; Tranchier, J.-P.; Mangeney, P. J. Org. Chem. 1992, 57, 4563-4565.
26. (e) Enders, D.; Tiebes, J. Liebigs Ann. Chem. 1993, 173-177.
27. 13. Fernández, R.; Gasch, C.; Lassaletta, J.-M.; Llera, J.-M.; Vázquez, J. Tetrahedron Lett. 1993, 34, 141-144.
28. 14. For recent asymmetric synthesis of cyanohydrins which do not rely on nucleophilic addition to aldehydes see: Enders, D.; Plant, A.; Backhaus, D.; Reinhold, U. Tetrahedron 1995, 39, 10699-10714 and references cited therein.
29. 15. (a) Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199-2204.
30. (b) Anh, N.T.; Eisenstein, O. Nouveau J. Chem. 1977, 1, 61-70.