Highly stereoselective aldol reaction for the synthesis of gamma-lactones starting from tartaric acid.
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.
Barros
M Teresa
MT
Departamento de Química, Faculdade de Ciências e Tecnologia da Universidade Nova de Lisboa, 2825-114 Monte da Caparica, Portugal.
Burke
Anthony J
AJ
Lou
Ji-Dong
JD
Maycock
Christopher D
CD
Wahnon
Jorge R
JR
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*
D004146:Dioxanes; D007783:Lactones; D018020:Lithium Compounds; D013644:Tartrates; C029768:tartaric acid