title: Highly diastereoselective lithium enolate aldol reactions of butane-2,3-diacetal desymmetrized glycolic acid and deprotection to enantiopure anti-2,3-dihydroxy esters.
abstract: [reaction--see text] The butane-2,3-diacetal (BDA) desymmetrized glycolic acid building block 1 undergoes efficient and highly diastereoselective lithium enolate aldol reactions with both aromatic and aliphatic aldehydes to afford, after an acidic methanolysis deprotection step, the enantiopure anti-2,3-dihydroxy esters in good yield.
authors.affiliation: Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK.
authors.forename: D J
authors.initials: DJ
authors.lastname: Dixon
authors.forename: S V
authors.initials: SV
authors.lastname: Ley
authors.forename: A
authors.initials: A
authors.lastname: Polara
authors.forename: T
authors.initials: T
authors.lastname: Sheppard
mesh_terms: D000080:Acetals; D000478:Alkylation; D002384:Catalysis; D004952:Esters; D007202:Indicators and Reagents; D008094:Lithium; D018020:Lithium Compounds; D012821:Silanes; D013237:Stereoisomerism
chemical_list: D000080:Acetals; D004952:Esters; D007202:Indicators and Reagents; D018020:Lithium Compounds; D012821:Silanes; C442342:butane-2,3-diacetal glycolic acid; D008094:Lithium; C442341:lithium hexamethyldisilazide