Diastereoselective alkylations of oxazolidinone glycolates: a useful extension of the Evans asymmetric alkylation.
[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.
Crimmins
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Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA. crimmins@email.unc.edu
Emmitte
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Katz
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D000478:Alkylation; D006016:Glycolates / Q000737:chemistry*; D006900:Hydroxylation; D010080:Oxazoles / Q000138:chemical synthesis*; D013237:Stereoisomerism
D006016:Glycolates; D010080:Oxazoles