title: Preparation of enantiopure butane-2,3-diacetals of glycolic acid and alkylation reactions leading to alpha-hydroxyacid and amide derivatives.
abstract: The preparation of butane-2,3-diacetal protected glycolic acid and related systems is described together with highly selective alkylation reactions of (R,R) and (S,S) butanediacetal protected glycolic acid. These compounds are readily deprotected to give enantiopure alpha-hydroxyacids, alpha-hydroxyesters or alpha-hydroxyamides by suitable choice of conditions.
authors.affiliation: Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, UK CB2 1EW. svl1000@cam.ac.uk
authors.forename: Steven V
authors.initials: SV
authors.lastname: Ley
authors.forename: Elena
authors.initials: E
authors.lastname: Diez
authors.forename: Darren J
authors.initials: DJ
authors.lastname: Dixon
authors.forename: Richard T
authors.initials: RT
authors.lastname: Guy
authors.forename: Patrick
authors.initials: P
authors.lastname: Michel
authors.forename: Gillian L
authors.initials: GL
authors.lastname: Nattrass
authors.forename: Tom D
authors.initials: TD
authors.lastname: Sheppard
mesh_terms: D000080:Acetals / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D006880:Hydroxy Acids / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D000080:Acetals; D000577:Amides; D006880:Hydroxy Acids; C442342:butane-2,3-diacetal glycolic acid