ENANTIOSELECTIVITY IN SYNTHESIS AND ALKYLATION OF HIGHLY SUBSTITUTED GAMMA-LACTONES - SEMIEMPIRICAL MODEL

Citation
Vs. Martin et al., ENANTIOSELECTIVITY IN SYNTHESIS AND ALKYLATION OF HIGHLY SUBSTITUTED GAMMA-LACTONES - SEMIEMPIRICAL MODEL, Anales de quimica, 89(1), 1993, pp. 85-88
Citations number
12
Categorie Soggetti
Chemistry
Journal title
ISSN journal
11302283
Volume
89
Issue
1
Year of publication
1993
Pages
85 - 88
Database
ISI
SICI code
1130-2283(1993)89:1<85:EISAAO>2.0.ZU;2-4
Abstract
The enantioselective synthesis of some gamma-lactones by an intramolec ular Michael type addition on alpha,beta-unsaturated esters is rationa lized by the relative thermodynamic stabilities of the possible final products, examined by semi-empirical methods. The structure of the alp ha-anion obtained by basic treatment permits the remarkable diastereos election shown by the alkylation to be understood. Free anions and che lated ones with metal sparkles or a lithium cation (MNDO) are analyzed as well as the possible solvent effects.