title: Stereoselective palladium-catalyzed functionalization of homoallylic alcohols: a convenient synthesis of di- and trisubstituted isoxazolidines and β-amino-δ-hydroxy esters.
abstract: Enantiopure, Boc-protected alkoxyamines 12 and 13, derived from the readily available homoallylic alcohols 4 via a reaction that involves either inversion or retention of configuration, undergo a diastereoselective Pd-catalyzed ring-closing carbonylative amidation to produce isoxazolidines 16/17 (≤50:1 diastereoisomer ratio (d.r.)) that can be readily converted into the N-Boc-protected esters of β-amino-δ-hydroxy acids and their γ-substituted homologues 37. The key carbonylative cyclization proceeds through an unusual syn addition of the palladium and the nitrogen nucleophile across the C=C bond (19→21), as revealed by the reaction of 15, which afforded isoxazolidine 18 with high diastereoselectivity.
authors.affiliation: Department of Chemistry, WestChem, University of Glasgow, Glasgow G12 8QQ, UK. a.malkov@lboro.ac.uk
authors.forename: Andrei V
authors.initials: AV
authors.lastname: Malkov
authors.forename: Maciej
authors.initials: M
authors.lastname: Barłóg
authors.forename: Lucie
authors.initials: L
authors.lastname: Miller-Potucká
authors.forename: Mikhail A
authors.initials: MA
authors.lastname: Kabeshov
authors.forename: Louis J
authors.initials: LJ
authors.lastname: Farrugia
authors.forename: Pavel
authors.initials: P
authors.lastname: Kočovský