title: Enantioselective synthesis of substituted piperidines by addition of aryl Grignard reagents to pyridine N-oxides.
abstract: The synthesis of optically active piperidines by enantioselective addition of aryl Grignard reagents to pyridine N-oxides and lithium binolate followed by reduction is reported for the first time. The reaction results in high yields (51-94%) in combination with good ee (54-80%). Some of these products were subsequently recrystallized, affording enhanced optical purities (>99% ee).
authors.affiliation: Department of Chemistry and Umeå Centre for Microbial Research, Umeå University, SE-90187 Umeå, Sweden.
authors.forename: Munawar
authors.initials: M
authors.lastname: Hussain
authors.forename: Thomas Sainte-Luce
authors.initials: TS
authors.lastname: Banchelin
authors.forename: Hans
authors.initials: H
authors.lastname: Andersson
authors.forename: Roger
authors.initials: R
authors.lastname: Olsson
authors.forename: Fredrik
authors.initials: F
authors.lastname: Almqvist
mesh_terms: D007202:Indicators and Reagents / Q000737:chemistry; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007202:Indicators and Reagents; D010880:Piperidines; D011725:Pyridines; C013229:pyridine N-oxide