title: An isothiourea-catalyzed asymmetric [2,3]-rearrangement of allylic ammonium ylides.
abstract: Benzotetramisole promotes the catalytic asymmetric [2,3]-rearrangement of allylic quaternary ammonium salts (either isolated or prepared in situ from p-nitrophenyl bromoacetate and the corresponding allylic amine), generating syn-α-amino acid derivatives with excellent diastereo- and enantioselectivity (up to >95:5 dr; up to >99% ee).
authors.affiliation: EaStCHEM, School of Chemistry, University of St Andrews , North Haugh, St Andrews KY16 9ST, U.K.
authors.forename: Thomas H
authors.initials: TH
authors.lastname: West
authors.forename: David S B
authors.initials: DS
authors.lastname: Daniels
authors.forename: Alexandra M Z
authors.initials: AM
authors.lastname: Slawin
authors.forename: Andrew D
authors.initials: AD
authors.lastname: Smith
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D064751:Ammonium Compounds / Q000737:chemistry*; D002384:Catalysis; D013237:Stereoisomerism; D013379:Substrate Specificity; D013890:Thiourea / Q000737:chemistry*
chemical_list: D000475:Alkenes; D064751:Ammonium Compounds; D013890:Thiourea