title: Stereocontrolled synthesis of vicinally functionalized piperidines by nucleophilic β-addition of alkyllithiums to α-aryl substituted piperidine enecarbamates.
abstract: Substituted piperidines are emerging as important medicinally-active structural motifs. Here, we report highly stereoselective carbolithiation reactions of α-aryl piperidine enecarbamates that offer direct access to vicinally-substituted piperidine compounds. We have also demonstrated that the carbanion intermediates can be trapped with a carbon electrophile.
authors.affiliation: Department of Chemistry, Susquehanna University, 514 University Avenue, Selinsgrove, PA 17870, USA.
authors.forename: Timothy K
authors.initials: TK
authors.lastname: Beng
authors.forename: Hironori
authors.initials: H
authors.lastname: Takeuchi
authors.forename: Manuel
authors.initials: M
authors.lastname: Weber
authors.forename: Richmond
authors.initials: R
authors.lastname: Sarpong
mesh_terms: D002219:Carbamates / Q000138:chemical synthesis* / Q000737:chemistry; D008094:Lithium / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D011789:Quantum Theory; D013237:Stereoisomerism
chemical_list: D002219:Carbamates; D009942:Organometallic Compounds; D010880:Piperidines; D008094:Lithium
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