title: Asymmetric Isothiourea-Catalysed Formal [3+2] Cycloadditions of Ammonium Enolates with Oxaziridines.
abstract: A highly enantioselective Lewis base-catalysed formal [3+2] cycloaddition of ammonium enolates and oxaziridines to give stereodefined oxazolidin-4-ones in high yield is described. Employing an enantioenriched oxaziridine in this process leads to a matched/mis-matched effect with the isothiourea catalyst and allowed the synthesis of either syn- or anti-stereodefined oxazolidin-4-ones in high d.r., yield and ee. Additionally, the oxazolidin-4-one products have been derivatised to afford functionalised enantioenriched building blocks.
authors.affiliation: EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST (UK).
authors.forename: Siobhan R
authors.initials: SR
authors.lastname: Smith
authors.affiliation: EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST (UK).
authors.forename: Charlene
authors.initials: C
authors.lastname: Fallan
authors.affiliation: EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST (UK).
authors.forename: James E
authors.initials: JE
authors.lastname: Taylor
authors.affiliation: EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST (UK).
authors.forename: Ross
authors.initials: R
authors.lastname: McLennan
authors.affiliation: EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST (UK).
authors.forename: David S B
authors.initials: DS
authors.lastname: Daniels
authors.affiliation: EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST (UK).
authors.forename: Louis C
authors.initials: LC
authors.lastname: Morrill
authors.affiliation: EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST (UK).
authors.forename: Alexandra M Z
authors.initials: AM
authors.lastname: Slawin
authors.affiliation: EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST (UK). ads10@st.andrews.ac.uk.
authors.forename: Andrew D
authors.initials: AD
authors.lastname: Smith
keywords: Lewis base; asymmetric synthesis; heterocycles; organocatalysis; oxaziridines