A SYNTHESIS OF ENANTIOMERICALLY ENRICHED PROPARGYL SILANES

Authors
FLEMING I MWANIKI JM
Citation
I. Fleming et Jm. Mwaniki, A SYNTHESIS OF ENANTIOMERICALLY ENRICHED PROPARGYL SILANES, Journal of the Chemical Society. Perkin transactions. I, (7), 1998, pp. 1237-1247
Citations number
37
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
7
Year of publication
1998
Pages
1237 - 1247
Database
ISI
SICI code
0300-922X(1998):7<1237:ASOEEP>2.0.ZU;2-D
Abstract
Reduction of ethyl 3-methyl-, 3-isopropyl- and 3-n-pentyl-3-[dimethyl( phenyl)silyl]propanoates 4 with DIBAL to the aldehydes 5, enol trifluo romethanesulfonate (triflate) formation using trifluoromethanesulfonic (triflic) anhydride and 2,6-di-tert-butylpyridine, and elimination us ing LDA, gives the propargyl silanes 8. The esters 4 could also be pre pared enantiomerically enriched (fl), and the final products are the e nantiomerically enriched propargyl (homochiral) silanes 14.