Regio- and stereoselective palladium(0)-catalyzed alkylation of vinyloxiranes with non-stabilized lithium ester enolates nucleophiles. A direct access to highly functionalized allylic alcohols

Tetrahedron Letters

Volumn 39, Issue 48, 1998, Pages 8849-8852

  Rychlet Elliott, Maryse ^a   Dhimane, Anne Lise ^a   Malacria, Max ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOL; ETHYLENE OXIDE DERIVATIVE; LITHIUM DERIVATIVE; PALLADIUM;

ALKYLATION; ARTICLE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032569860     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/s0040-4039(98)02027-9     Document Type: Article

References (19)

1. 1 Rychlet Elliott M., Dhimane A-L., Malacria M. J. Am. Chem. Soc. 1997, 119, 3427-3428.
2. 2 (a) Tsuji J., Kataoka H., Kobayashi Y. Tetrahedron Lett. 1981, 22, 2575-2578.
3. (b). Trost B. M., Molander G. A. J. Am. Chem. Soc. 1981, 103, 5969-5972.
4. (c) Tsuda T., Tokai M., Ishida T., Saegusa T. J. Org. Chem. 1986, 57, 5216-5221.
5. (d) Tsuji J. Tetrahedron 1986, 42, 4361-4401.
6. 3. For addition of ketone enolates to π-allylpalladium compounds, see a) Akermark B. Jutand A. J. Organomet. Chem. 1981, 217, C41-C43,
7. b) Fiaud J.C., Malleron J.L. J. Chem. Soc. Chem. Comm. 1981, 1159-1160.
8. 4. Tsuji J. Pure and Appl. Chem. 1986, 58, 869-878.
9. 5. Trost B.M., Scanlan T.S. J. Am. Chem. Soc. 1989, 111, 4988-4990
10. 6. Tarnchompoo B., Thebtaranonth C., Thebtaranonth Y. Tetrahedron Lett. 1987, 28, 6671-6674.
11. 3-allyl) iron complexes opposed to silylketene acetals has been described to efficiently yield a diester equivalent: Enders D., Frank U., Fey P., Jandeleit B., Lohray B. B. J. Organomet. Chem. 1996, 519, 147-159.
12. Otherwise, radical approaches including the radical addition of methyl acetate to vinyloxiranes catalyzed by amine-boranes produces the allylic alcohol via an oxiranyl carbinyl radical. Yields are average from cyclic epoxides but very poor from more flexible acyclic ones: Dang H., Roberts B.P. Tetrahedron Lett. 1992, 33, 6169-6172.
13. 8 (a) Sternbach D. D., Ensinger C. L. J. Org. Chem. 1990, 55, 2725-2736;
14. (b) Crimmins M.T., Mascarella S. W., DeLoach J. A. J. Org. Chem. 1984, 49, 3033-3035.
15. 9. 1a was prepared according: Reist E. J., Junga I.G., Baker B.R. J. Org. Chem. 1960, 25, 1673-1674. 1b is commercially available. 1c was directly prepared by classical mCPBA epoxidation. 1d was prepared by Wittig reaction from the corresponding α,β-epoxyketone.
16. 10. Starting from the α-monosubstituted enolate of ethyl propanoate, we could not isolate the expected adduct among the numerous compounds formed. Probably competitive over-alkylation occured.
17. 3), thus confirming the cis relationship between both substituents of cyclooctenes 8 to 10.
18. 12. Ziegler F.E., Mencel J. J. Tetrahedron Lett. 1984, 25, 123-126.
19. 3 : C, 69.96; H, 10.06. Found : C, 69.87; H, 10.12.