title: Diastereoselective magnesium halide-catalyzed anti-aldol reactions of chiral N-acyloxazolidinones.
abstract: A chiral auxilliary-based direct aldol reaction is reported. The reactions are catalytic in magnesium salts and are facilitated by silylation with chlorotrimethylsilane. The adducts isolated are in high diastereoselectivity (up to 32:1 dr) and favor the anti-aldol diastereomer B. Reactions are operationally simple and can be run under ambient atmosphere without rigorous exclusion of water. Many of the adducts are highly crystalline and a single diastereomer can be isolated without chromatography.
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
authors.forename: David A
authors.initials: DA
authors.lastname: Evans
authors.forename: Jason S
authors.initials: JS
authors.lastname: Tedrow
authors.forename: Jared T
authors.initials: JT
authors.lastname: Shaw
authors.forename: C Wade
authors.initials: CW
authors.lastname: Downey
mesh_terms: D001547:Benzaldehydes / Q000737:chemistry; D002384:Catalysis; D015636:Magnesium Chloride / Q000737:chemistry*; D023303:Oxazolidinones / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001547:Benzaldehydes; D023303:Oxazolidinones; D015636:Magnesium Chloride; C032175:benzaldehyde