title: Isothiourea-mediated asymmetric O- to C-carboxyl transfer of oxazolyl carbonates: structure-selectivity profiles and mechanistic studies.
abstract: The structural motif within a series of tetrahydropyrimidine-based isothioureas necessary for generating high asymmetric induction in the asymmetric Steglich rearrangement of oxazolyl carbonates is fully explored, with crossover and dynamic (19)F NMR experiments used to develop a mechanistic understanding of this transformation.
authors.affiliation: EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST, United Kingdom.
authors.forename: Caroline
authors.initials: C
authors.lastname: Joannesse
authors.forename: Craig P
authors.initials: CP
authors.lastname: Johnston
authors.forename: Louis C
authors.initials: LC
authors.lastname: Morrill
authors.forename: Philip A
authors.initials: PA
authors.lastname: Woods
authors.forename: Madeleine
authors.initials: M
authors.lastname: Kieffer
authors.forename: Tobias A
authors.initials: TA
authors.lastname: Nigst
authors.forename: Herbert
authors.initials: H
authors.lastname: Mayr
authors.forename: Tomas
authors.initials: T
authors.lastname: Lebl
authors.forename: Douglas
authors.initials: D
authors.lastname: Philp
authors.forename: Ryan A
authors.initials: RA
authors.lastname: Bragg
authors.forename: Andrew D
authors.initials: AD
authors.lastname: Smith
mesh_terms: D002254:Carbonates / Q000737:chemistry*; D002384:Catalysis; D058115:Lewis Bases / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry*; D011743:Pyrimidines / Q000737:chemistry*; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry*
chemical_list: D002254:Carbonates; D058115:Lewis Bases; D010080:Oxazoles; D011743:Pyrimidines; D013890:Thiourea