title: Asymmetric conjugate addition of alkylzirconium reagents to α,β-unsaturated lactones.
abstract: The asymmetric synthesis of β-substituted lactones by catalytic asymmetric conjugate addition of alkyl groups to α,β-unsaturated lactones is reported. The method uses alkylzirconium nucleophiles prepared in situ from alkenes and the Schwartz reagent. Enantioselective additions to 6- and 7-membered lactones proceed at rt, tolerate a wide variety of functional groups, and are readily scalable. The method was used in a formal asymmetric synthesis of mitsugashiwalactone.
authors.affiliation: Department of Chemistry, Chemistry Research Laboratory, University of Oxford , 12 Mansfield Road, Oxford, OX1 3TA, U.K.
authors.forename: Eleanor E
authors.initials: EE
authors.lastname: Maciver
authors.forename: Rebecca M
authors.initials: RM
authors.lastname: Maksymowicz
authors.forename: Nancy
authors.initials: N
authors.lastname: Wilkinson
authors.forename: Philippe M C
authors.initials: PM
authors.lastname: Roth
authors.forename: Stephen P
authors.initials: SP
authors.lastname: Fletcher