ELIMINATION VERSUS DIASTEREOSELECTIVE ALKYLATION IN HOMOCHIRAL 2-(BETA-ETHOXY CARBONYL) ACETALS

Authors
CABALLERO M GARCIAVALVERDE M PEDROSA R VICENTE M
Citation
M. Caballero et al., ELIMINATION VERSUS DIASTEREOSELECTIVE ALKYLATION IN HOMOCHIRAL 2-(BETA-ETHOXY CARBONYL) ACETALS, Tetrahedron : asymmetry, 7(1), 1996, pp. 219-226
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
7
Issue
1
Year of publication
1996
Pages
219 - 226
Database
ISI
SICI code
0957-4166(1996)7:1<219:EVDAIH>2.0.ZU;2-F
Abstract
The reaction of the homochiral 2-(beta-ethoxycarbonyl) dioxolane deriv ed from (-)-exo-camphanediol with methyl iodide in the presence of one equivalent of LDA lead to the alkylated product in very good chemical yield and poor diastereomeric excess. 2-(beta-Ethoxycarbonyl)-1,3-dio xanes derived from 2,4-pentanediol behave in a different way, whereas the diequatorial form is alkylated in excellent chemical yield, the eq uatorial-axial diastereoisomer yields a mixture of alkylation and elim ination products.