title: Highly stereoselective aldol reaction for the synthesis of gamma-lactones starting from tartaric acid.
abstract: A simple stereoselective process for the synthesis of highly substituted gamma-lactones was developed based on aldol reactions between the enolate of dioxanes derived from tartaric acid and aldehydes. A range of aromatic and aliphatic aldehydes were reacted, in most cases achieving good yields and stereoselectivity. The limitations of this reaction were identified and a transition state is proposed.
authors.affiliation: Departamento de Química, Faculdade de Ciências e Tecnologia da Universidade Nova de Lisboa, 2825-114 Monte da Caparica, Portugal.
authors.forename: M Teresa
authors.initials: MT
authors.lastname: Barros
authors.forename: Anthony J
authors.initials: AJ
authors.lastname: Burke
authors.forename: Ji-Dong
authors.initials: JD
authors.lastname: Lou
authors.forename: Christopher D
authors.initials: CD
authors.lastname: Maycock
authors.forename: Jorge R
authors.initials: JR
authors.lastname: Wahnon
mesh_terms: D002384:Catalysis; D004146:Dioxanes / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis*; D018020:Lithium Compounds / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013644:Tartrates / Q000737:chemistry*
chemical_list: D004146:Dioxanes; D007783:Lactones; D018020:Lithium Compounds; D013644:Tartrates; C029768:tartaric acid