Stereoconvergent preparation of chiral vinylsilanes by cuprate substitution of α-acetoxyallylsilanes. Application to the synthesis of (S)-(+)-bishomomanicone

Tetrahedron

Volumn 59, Issue 38, 2003, Pages 7527-7533

  Guintchin, Boris ^a   Bienz, Stefan ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

(S) (+) bishomomanicone; Chiral vinylsilanes; Stereoconvergent; acetoxyallylsilanes

Indexed keywords

1 [[(2 METHOXY 2 PHENYLETHOXY)METHYL]DIMETHYLSILYL] 1 METHYLBUT 2 ENYLACETATE; 1,3 DIMETHYLHEPT 1 ENYL[(2 METHOXY 2 PHENYLETHOXY)METHYL]DIMETHYLSILANE; 2 [[(2 METHOXY 2 PHENYLETHOXY)METHYL]DIMETHYLSILYL]PENT 3 EN 2 OL; ACETIC ACID DERIVATIVE; ACYLSILANE; ALLYL COMPOUND; BISHOMOMANICONE; KETONE DERIVATIVE; SILANE DERIVATIVE; SILICON; UNCLASSIFIED DRUG; [(2 METHOXY 2 PHENYLETHOXY)METHYL]DIMETHYL 1 METHYL 3 PHENYLBUT 1 ENYLSILANE;

ARTICLE; CHIRALITY; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 0041829482     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)01169-4     Document Type: Article

References (26)

1. Koch P., Kunz R.W., Bienz S. Mol. Online. 3:1999;9.
2. Enev V., Stojanova D., Bienz S. Helv. Chim. Acta. 79:1996;391.
3. Fässler J., Enev V., Bienz S. Helv. Chim. Acta. 82:1999;561.
4. Fässler J., Linden A., Bienz S. Tetrahedron. 55:1999;1717.
5. Bienz S., Enev V., Huber P. Tetrahedron Lett. 35:1994;1161.
6. Gassmann S., Guintchin B., Bienz S. Organometallics. 20:2001;1849.
7. Bestmann H.J., Attygalle A.B., Glasbrenner J., Riemer R., Vostrowsky O., Constantino M.G., Melikian G., Morgan E.D. Ann. Chem. 1988;55.
8. Corbier B., Teisseire P. Recherches. 19:1974;291.
9. Bratovanov S., Bienz S. Tetrahedron: Asymmetry. 8:1997;1587.
10. Fleming I., Thomas A.P. J. Chem. Soc., Chem. Commun. 1986;1456.
11. Corey E.J., Boaz N.W. Tetrahedron Lett. 25:1984;3063.
12. Spino C., Beaulieu C., Lafrenière J. J. Org. Chem. 65:2000;7091.
13. Fleming I., Dunogues J., Smithers R. Org. React. 37:1989;57.
14. Chou S.S.P., Kuo H.L., Wang C.J., Tsai C.Y., Sun C.M. J. Org. Chem. 54:1989;868.
15. Terashima S., Tseng C.C., Koga K. Chem. Pharm. Bull. 27:1979;747.
16. Levene P.A., Bass L.W. J. Biol. Chem. 70:1926;211.
17. Lubell W.D., Jamison T.F., Rapoport H. J. Org. Chem. 55:1990;3511.
18. Levene P.A., Mikeska L.A. J. Biol. Chem. 84:1929;571.
19. Kumar I., Manju K., Jolly R.S. Tetrahedron: Asymmetry. 12:2001;1431.
20. Tandon V.K. Tetrahedron Lett. 42:2001;5985.
21. Carde L., Davies D.H., Roberts S.M. J. Chem. Soc. Perkin Trans. 1. 2000;2455.
22. Hamman S., Michals D.R., Pickard S.T., Smith H.E. J. Fluorine Chem. 62:1993;131.
23. Senanayake C.H., Bill T.J., Larsen R.D., Leazer J., Reider P.J. Tetrahedron Lett. 33:1992;5901.
24. Lubell W.D., Rapoport H. J. Am. Chem. Soc. 110:1988;7447.
25. Nakagaki R., Takahira O., Yamaoka M., Kashima N. Bull. Chem. Soc. Jpn. 68:1995;2803.
26. Dale J.A., Mosher H.S. J. Am. Chem. Soc. 95:1973;512.