title: Isothiourea-catalysed asymmetric C-acylation of silyl ketene acetals.
abstract: Screening of a range of chiral isothioureas and acyl donors to promote the asymmetric C-acylation of silyl ketene acetals indicates that C(2)-aryl-dihydropyrimidobenzothiazole-derived isothioureas and propionic anhydride give optimal reactivity and enantioselectivity in this process. Under optimised conditions 3-acyl-3-aryl or 3-acyl-3-alkylfuranones are prepared in good yields and moderate to excellent enantioselectivities (up to 98% ee; ee=enantiomeric excess).
authors.affiliation: Department EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, UK.
authors.forename: Philip A
authors.initials: PA
authors.lastname: Woods
authors.forename: Louis C
authors.initials: LC
authors.lastname: Morrill
authors.forename: Ryan A
authors.initials: RA
authors.lastname: Bragg
authors.forename: Andrew D
authors.initials: AD
authors.lastname: Smith
mesh_terms: D000080:Acetals / Q000737:chemistry*; D000215:Acylation; D002384:Catalysis; D005030:Ethylenes / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry*
chemical_list: D000080:Acetals; D005030:Ethylenes; D005663:Furans; D007659:Ketones; D012821:Silanes; D013890:Thiourea; C008223:ketene