ENANTIORETENTIVE ALKYLATION OF OXAZOLIDINONE ALUMINUM ENOLATES WITH EPOXIDES - PREPARATION OF UNCODED HOMOSERINE ANALOGS

Authors
SMITH AB PASTERNAK A YOKOYAMA A HIRSCHMANN R
Citation
Ab. Smith et al., ENANTIORETENTIVE ALKYLATION OF OXAZOLIDINONE ALUMINUM ENOLATES WITH EPOXIDES - PREPARATION OF UNCODED HOMOSERINE ANALOGS, Tetrahedron letters, 35(48), 1994, pp. 8977-8980
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
48
Year of publication
1994
Pages
8977 - 8980
Database
ISI
SICI code
0040-4039(1994)35:48<8977:EAOOAE>2.0.ZU;2-I
Abstract
The alkylation of Karady/Seebach oxazolidinone enolates with epoxides, promoted by 2.1 equivalents of diethylaluminum chloride, furnishes ri ng-opened adducts in moderate-to-good yields with high diastereoselect ivity. The method provides an effective approach to uncoded homoserine analogs and expands the utility of readily available oxazolidinones i n asymmetric synthesis.