Practical synthesis of bis-homoallylic alcohols from dialdehydes or their acetals

Tetrahedron Letters

Volumn 43, Issue 36, 2002, Pages 6329-6330

  Samoshin, Vyacheslav V ^a   Gremyachinskiy, Dmitriy E ^a   Smith, Lori L ^a   Bliznets, Igor V ^a   Gross, Paul H ^a  

^a UNIVERSITY OF THE PACIFIC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; DIALDEHYDE; POTASSIUM IODIDE; TIN CHLORIDE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL PARAMETERS; CHEMICAL PROCEDURES; SYNTHESIS;

EID: 0037009685     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01398-9     Document Type: Article

References (31)

1. Li C.-J., Chan T.-H. Organic Reactions in Aqueous Media. 1997;John Wiley and Sons, New York.
2. Li C.-J., Chen D.-L., Lu Y.-Q., Haberman J.X., Mague J.T. Tetrahedron. 54:1998;2347-2364.
3. Chen G.-M., Brown H.C., Ramachandran P.V. J. Org. Chem. 64:1999;721-725.
4. Baylon C., Heck M.-P., Mioskowski C. J. Org. Chem. 64:1999;3354-3360.
5. Zhang W.-C., Li C.-J. Tetrahedron. 56:2000;2403-2411.
6. Jaber J.J., Mitsui K., Rychnovsky S.D. J. Org. Chem. 66:2001;4679-4686.
7. Balskus E.P., Mendez-Andino J., Arbit R.M., Paquette L.A. J. Org. Chem. 66:2001;6695-6704.
8. Ramachandran P.V. Aldrichim. Acta. 35:2002;23-35.
9. Ramachandran P.V., Chen G.-M., Brown H.C. Tetrahedron Lett. 38:1997;2417-2420.
10. Chen G.-M., Ramachandran P.V. Tetrahedron: Asymmetry. 8:1997;3935-3938.
11. Marvell E.N., Cheng J.C.-P. J. Org. Chem. 45:1980;4511-4514.
12. Masuyama Y., Tsunoda T., Kurusu Y. Chem. Lett. 1989;1647-1650.
13. Gewald R., Kira M., Sakurai H. Synthesis. 1996;111-115.
14. Hoffmann R.W., Kahrs B.C. Tetrahedron Lett. 37:1996;4479-4482.
15. Rychnovsky S.D., Griesgraber G., Zeller S., Skalitzky D.J. J. Org. Chem. 56:1991;5161-5169.
16. Gómez-Sánchez A., Hermosin I., Lassaletta J.-M., Maya I. Tetrahedron. 49:1993;1237-1250.
17. Li C.-J. Green Chem. 4:2002;1-4.
18. Einhorn C., Luche J.-L. J. Organomet. Chem. 322:1987;177-183.
19. Wang D., Chen D., Haberman J.X., Li C.-J. Tetrahedron. 54:1998;5129-5142.
20. Wilson S.R., Guazzaroni M.E. J. Org. Chem. 54:1989;3087-3091.
21. Yanagisawa A., Inoue H., Morodome M., Yamamoto H. J. Am. Chem. Soc. 115:1993;10356-10357.
22. Hachiya I., Kobayashi S. J. Org. Chem. 58:1993;6958-6960.
23. Marton D., Stivanello D., Tagliavini G. J. Organomet. Chem. 540:1997;77-81.
24. Chan T.H., Yang Y., Li C.-J. J. Org. Chem. 64:1999;4452-4455.
25. Petrier C., Luche J.-L. J. Org. Chem. 50:1985;910-912.
26. Houllemare D., Outurquin F., Paulmier C. J. Chem. Soc., Perkin Trans. 1. 1997;1629-1632.
27. Samoshin V.V., Gremyachinskiy D.E., Gross P.H. Mendeleev Commun. 1999;53.
28. 2 (Marton, D.; Stivanello, D.; Tagliavini, G. J. Org. Chem. 1996, 61, 2731-2737). See also Ref. 18.
29. 2 (Marton, D.; Stivanello, D.; Tagliavini, G. J. Org. Chem. 1996, 61, 2731-2737). See also Ref. 18.
30. Transformation of acetals into homoallylic alcohols by treatment with either trifluoroacetic acid or silica gel followed by tetraallyltin has been reported: McCluskey A., Mayer D.M., Young D.J. Tetrahedron Lett. 38:1997;5217-5218.
31. Indium mediated allylation of benzaldehyde and cinnamaldehyde dimethylacetals with allylic bromides in aq. THF has been described recently; aliphatic acetals were unreactive: Kwon J.S., Pae A.N., Choi K.I., Koh H.Y., Kim Y., Cho Y.S. Tetrahedron Lett. 42:2001;1957-1959.