title: Asymmetric synthesis of highly substituted β-lactones through oxidative carbene catalysis with LiCl as cooperative Lewis acid.
abstract: The reaction of enals with β-diketones, β-ketoesters, and malonates bearing a β-oxyalkyl substituent at the α-position by oxidative NHC catalysis to provide highly substituted β-lactones is described. Reactions occur with excellent diastereo- and enantioselectivity. The organo cascade comprises two CC bond formations and one CO bond formation. Up to four contiguous stereogenic centers including two fully substituted stereocenters are formed in the cascade.
authors.affiliation: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster (Germany).
authors.forename: Srikrishna
authors.initials: S
authors.lastname: Bera
authors.forename: Ramesh C
authors.initials: RC
authors.lastname: Samanta
authors.forename: Constantin G
authors.initials: CG
authors.lastname: Daniliuc
authors.forename: Armido
authors.initials: A
authors.lastname: Studer
mesh_terms: D002384:Catalysis; D003510:Cyclohexanes / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis*; D058116:Lewis Acids / Q000737:chemistry*; D018021:Lithium Chloride / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D016877:Oxidants / Q000737:chemistry; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D003510:Cyclohexanes; D007783:Lactones; D058116:Lewis Acids; D016877:Oxidants; C030011:carbene; D018021:Lithium Chloride; D008697:Methane
keywords: N-heterocyclic carbenes; asymmetric synthesis; cooperative catalysis; organo catalysis; β-lactones