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

TY - JOUR

T1 - Regio- and Stereoselective Alkylation of Pyridine-N-oxides

T2 - Synthesis of Substituted Piperidines and Pyridines

AU - Barange, Deepak Kumar

AU - Johnson, Magnus T.

AU - Cairns, Andrew G.

AU - Olsson, Roger

AU - Almqvist, Fredrik

PY - 2016/12/16

Y1 - 2016/12/16

N2 - 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.

AB - 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.

KW - Reagents

KW - Stereoselectivity

KW - Electrophiles

KW - Alkyls

KW - Piperidines

UR - https://www.scopus.com/pages/publications/85006474723

U2 - 10.1021/acs.orglett.6b02667

DO - 10.1021/acs.orglett.6b02667

M3 - Article

AN - SCOPUS:85006474723

SN - 1523-7060

VL - 18

SP - 6228

EP - 6231

JO - Organic Letters

JF - Organic Letters

IS - 24

ER -