Publication
Title
Removal of the pyridine directing group from -substituted N-(pyridin-2-yl)piperidines obtained via directed Ru-catalyzed C-H functionalization
Author
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.
Language
English
Source (journal)
The journal of organic chemistry. - Washington, D.C.
Publication
Washington, D.C. : 2013
ISSN
0022-3263
Volume/pages
78:19(2013), p. 9803-9814
ISI
000326320100025
Full text (Publishers DOI)
Full text (publishers version - intranet only)
UAntwerpen
Faculty/Department
Research group
Publication type
Subject
Affiliation
Publications with a UAntwerp address
External links
Web of Science
Record
Identification
Creation 20.01.2014
Last edited 17.05.2017
To cite this reference