title: Diastereoselective alkylations of oxazolidinone glycolates: a useful extension of the Evans asymmetric alkylation.
abstract: [reaction: see text] The diastereoselective alkylation of glycolate oxazolidinones has been demonstrated as a method for the enantioselective preparation of alpha-alkoxy carboxylic acid derivatives and selectively protected 1,2-diols. Various protecting groups on the glycolate hydroxyl and multiple substitution patterns on allylic iodides are tolerated in the alkylation. Yields for the alkylations are typically 70-85% with diastereoselectivities of >98:2.
authors.affiliation: Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA. crimmins@email.unc.edu
authors.forename: M T
authors.initials: MT
authors.lastname: Crimmins
authors.forename: K A
authors.initials: KA
authors.lastname: Emmitte
authors.forename: J D
authors.initials: JD
authors.lastname: Katz
mesh_terms: D000478:Alkylation; D006016:Glycolates / Q000737:chemistry*; D006900:Hydroxylation; D010080:Oxazoles / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D006016:Glycolates; D010080:Oxazoles