Regio- and Stereoselective Alkylation of Pyridine-N-oxides: Synthesis of Substituted Piperidines and Pyridines

• DOI: 10.1021/acs.orglett.6b02667
• Publication Date: 2016-11-28T20:04:52Z
• Authors: Deepak Kumar Barange; Magnus T. Johnson; Andrew G. Cairns; Roger Olsson; Fredrik Almqvist
• Keywords: /dk/atira/pure/subjectarea/asjc/1600/1606; /dk/atira/pure/subjectarea/asjc/1300/1303; Reagents; /dk/atira/pure/subjectarea/asjc/1600/1605; name=Biochemistry; Stereoselectivity; Electrophiles; 540; 01 natural sciences; Alkyls; 0104 chemical sciences; Piperidines; name=Organic Chemistry; name=Physical and Theoretical Chemistry

Regio- and stereoselective addition of alkyl Grignard reagents to pyridine-N-oxides gave C2-alkylated N-hydroxy-1,2,5,6-tetrahydropyridines trans-2,3-disubstituted in good excellent yields. These intermediates were aromatized or alternatively reduced one-pot methodologies for efficient syntheses alkylpyridines piperidines, respectively. reactions have a broad substrate scope short reaction times.