title: N-heterocyclic carbene-catalyzed Ireland-Coates Claisen rearrangement: synthesis of functionalized β-lactones.
abstract: The N-heterocyclic carbene (NHC)-catalyzed Claisen rearrangement of hybrid Ireland-Coates structures has been achieved, allowing the stereoselective synthesis of highly functionalized β-lactones. The reaction proceeds with high diastereoselectivity (>20:1) and affords a diverse range of β-lactone fused cyclopentanes. Mechanistic studies are detailed.
authors.affiliation: School of Chemistry, Monash University, Clayton, Victoria 3800, Australia.
authors.forename: Lisa
authors.initials: L
authors.lastname: Candish
authors.forename: David W
authors.initials: DW
authors.lastname: Lupton
mesh_terms: D002384:Catalysis; D006571:Heterocyclic Compounds / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D006571:Heterocyclic Compounds; D007783:Lactones; C030011:carbene; D008697:Methane