Title
Removal of the pyridine directing group from <tex>$\alpha$</tex>-substituted N-(pyridin-2-yl)piperidines obtained via directed Ru-catalyzed <tex>$sp^{3}$</tex> C-H functionalization Removal of the pyridine directing group from <tex>$\alpha$</tex>-substituted N-(pyridin-2-yl)piperidines obtained via directed Ru-catalyzed <tex>$sp^{3}$</tex> C-H functionalization
Author
Faculty/Department
Faculty of Sciences. Chemistry
Faculty of Applied Engineering Sciences
Publication type
article
Publication
Washington, D.C. ,
Subject
Chemistry
Source (journal)
The journal of organic chemistry. - Washington, D.C.
Volume/pages
78(2013) :19 , p. 9803-9814
ISSN
0022-3263
ISI
000326320100025
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
Affiliation
University of Antwerp
Abstract
Two strategies, hydrogenationhydride reduction and quaternizationhydride reduction, are reported that make use of mild reaction conditions (room temperature) to efficiently remove the N-pyridin-2-yl directing group from a diverse set of C-2-substituted piperidines that were synthesized through directed Ru-catalyzed sp3 CH functionalization. The deprotected products are obtained in moderate to good overall yields irrespective of the strategy followed, indicating that both methods are generally equally effective. Only in the case of 2,6-disubstituted piperidines, could the quaternizationhydride reduction strategy not be used. The hydrogenationhydride reduction protocol was successfully applied to trans- and cis-2-methyl-N-(pyridin-2-yl)-6-undecylpiperidine in a short synthetic route toward (±)-solenopsin A (trans diastereoisomer) and (±)-isosolenopsin A (cis diastereoisomer). The absolute configuration of the enantiomers of these fire ant alkaloids could be determined via VCD spectroscopy.
E-info
https://repository.uantwerpen.be/docman/iruaauth/dcd4ab/ec6d6cb95af.pdf
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