title: Regio- and Stereoselective Alkylation of Pyridine-N-oxides: Synthesis of Substituted Piperidines and Pyridines.
abstract: Regio- and stereoselective addition of alkyl Grignard reagents to pyridine-N-oxides gave C2-alkylated N-hydroxy-1,2,5,6-tetrahydropyridines and trans-2,3-disubstituted N-hydroxy-1,2,5,6-tetrahydropyridines in good to excellent yields. These intermediates were aromatized or alternatively reduced in one-pot methodologies for efficient syntheses of alkylpyridines or piperidines, respectively. These reactions have a broad substrate scope and short reaction times.
authors.affiliation: Department of Chemistry, Umeå University , 90187 Umeå, Sweden.
authors.forename: Deepak Kumar
authors.initials: DK
authors.lastname: Barange
authors.affiliation: Centre for Analysis and Synthesis, Lund University , 22100 Lund, Sweden.
authors.forename: Magnus T
authors.identifier: 0000-0002-2547-9842
authors.initials: MT
authors.lastname: Johnson
authors.affiliation: Department of Chemistry, Umeå University , 90187 Umeå, Sweden.
authors.forename: Andrew G
authors.initials: AG
authors.lastname: Cairns
authors.affiliation: Chemical Biology & Therapeutic Unit, Department of Experimental Medical Science, Lund University , 22100 Lund, Sweden.
authors.forename: Roger
authors.initials: R
authors.lastname: Olsson
authors.affiliation: Department of Chemistry, Umeå University , 90187 Umeå, Sweden.
authors.forename: Fredrik
authors.identifier: 0000-0003-4646-0216
authors.initials: F
authors.lastname: Almqvist