title: Synthesis and kinetic resolution of N-Boc-2-arylpiperidines.
abstract: The chiral base n-BuLi/(-)-sparteine or n-BuLi/(+)-sparteine surrogate promotes kinetic resolution of N-Boc-2-arylpiperidines by asymmetric deprotonation. The enantioenriched starting material was recovered with yields 39-48% and ers up to 97 : 3. On lithiation then electrophilic quench, 2,2-disubstituted piperidines were obtained with excellent yields and enantioselectivities.
authors.affiliation: Department of Chemistry, University of Sheffield, Sheffield, S3 7HF, UK. i.coldham@sheffield.ac.uk.
authors.forename: Edward J
authors.initials: EJ
authors.lastname: Cochrane
authors.forename: Daniele
authors.initials: D
authors.lastname: Leonori
authors.forename: Lorraine A
authors.initials: LA
authors.lastname: Hassall
authors.forename: Iain
authors.initials: I
authors.lastname: Coldham
mesh_terms: D007700:Kinetics; D009942:Organometallic Compounds / Q000737:chemistry*; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013034:Sparteine / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D009942:Organometallic Compounds; D010880:Piperidines; C434823:n-butyllithium; D013034:Sparteine