Enantioselective Synthesis of Chiral Piperidines via the Stepwise Dearomatization/Borylation of Pyridines
Division
of Chemical Process
Engineering, Graduate School of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan
of Chemical Process
Engineering, Graduate School of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan
J. Am. Chem. Soc., Article ASAP
DOI: 10.1021/jacs.6b01375
Publication Date (Web): March 11, 2016
Copyright © 2016 American Chemical Society
Abstract
We
have developed a novel approach for the synthesis of enantioenriched
3-boryl-tetrahydropyridines via the Cu(I)-catalyzed regio-, diastereo-,
and enantioselective protoborylation of 1,2-dihydropyridines, which were
obtained by the partial reduction of the pyridine derivatives. This
dearomatization/enantioselective borylation stepwise strategy provides
facile access to chiral piperidines together with the stereospecific
transformation of a stereogenic C–B bond from readily available starting
materials. Furthermore, the utility of this method is demonstrated for
the concise synthesis of the antidepressant drug (−)-paroxetine. A
theoretical study of the reaction mechanism is also described.
have developed a novel approach for the synthesis of enantioenriched
3-boryl-tetrahydropyridines via the Cu(I)-catalyzed regio-, diastereo-,
and enantioselective protoborylation of 1,2-dihydropyridines, which were
obtained by the partial reduction of the pyridine derivatives. This
dearomatization/enantioselective borylation stepwise strategy provides
facile access to chiral piperidines together with the stereospecific
transformation of a stereogenic C–B bond from readily available starting
materials. Furthermore, the utility of this method is demonstrated for
the concise synthesis of the antidepressant drug (−)-paroxetine. A
theoretical study of the reaction mechanism is also described.
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