title: Enantioselective acylation of silyl ketene acetals through fluoride anion-binding catalysis.
abstract: A highly enantioselective acylation of silyl ketene acetals with acyl fluorides has been developed to generate useful α,α-disubstituted butyrolactone products. This transformation is promoted by a new thiourea catalyst and 4-pyrrolidinopyridine and represents the first example of enantioselective thiourea anion-binding catalysis with fluoride.
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, United States.
authors.forename: James A
authors.initials: JA
authors.lastname: Birrell
authors.forename: Jean-Nicolas
authors.initials: JN
authors.lastname: Desrosiers
authors.forename: Eric N
authors.initials: EN
authors.lastname: Jacobsen
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D000080:Acetals / Q000737:chemistry*; D000215:Acylation; D000838:Anions / Q000737:chemistry; D002384:Catalysis; D005030:Ethylenes / Q000737:chemistry*; D005459:Fluorides / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000080:Acetals; D000838:Anions; D005030:Ethylenes; D007659:Ketones; C008223:ketene; D015107:4-Butyrolactone; D005459:Fluorides