title: Direct catalytic asymmetric synthesis of highly functionalized tetronic acids/tetrahydro-isobenzofuran-1,5-diones via combination of cascade three-component reductive alkylations and Michael-aldol reactions.
abstract: A practical and sustainable chemical process for the synthesis of highly substituted tetrahydro-isobenzofuran-1,5-diones was achieved for the first time through asymmetric cascade Michael-aldol reaction of 4-hydroxy-3-alkyl-5H-furan-2-ones with alkyl vinyl ketones in the presence of a catalytic amount of l-proline or 9-amino-9-deoxyepiquinine/TCA. In this article, we discovered for the first time the asymmetric synthesis of privileged bicyclic lactones through kinetic resolution and show the synthetic application to pharmaceuticals and natural products synthesis.
authors.affiliation: School of Chemistry, University of Hyderabad, Hyderabad-500 046, India. ramsc@uohyd.ernet.in
authors.forename: Dhevalapally B
authors.initials: DB
authors.lastname: Ramachary
authors.forename: Mamillapalli
authors.initials: M
authors.lastname: Kishor
mesh_terms: D000478:Alkylation; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D011392:Proline / Q000737:chemistry; D011807:Quinolizines / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C517737:9-amino-9-deoxyepiquinine; D001572:Benzofurans; D011807:Quinolizines; D011392:Proline