Removal of the Pyridine Directing Group from α-Substituted N-(Pyridin-2-yl)piperidines Obtained via Directed Ru-Catalyzed sp3 C–H Functionalization
作者： Veerle Smout , Aldo Peschiulli , Stefan Verbeeck , Emily A. Mitchell , Wouter Herrebout
DOI: 10.1021/JO401521Y
关键词:
摘要: Two strategies, “hydrogenation–hydride reduction” and “quaternization–hydride 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 C-2-substituted piperidines were synthesized through directed Ru-catalyzed sp3 C–H functionalization. The deprotected products obtained in moderate good overall yields irrespective strategy followed, indicating both methods generally equally effective. Only case 2,6-disubstituted piperidines, could not be used. protocol was successfully applied trans- cis-2-methyl-N-(pyridin-2-yl)-6-undecylpiperidine short synthetic route toward (±)-solenopsin A (trans diastereoisomer) (±)-isosolenopsin (cis diastereoisomer). absolute configuration enantiomers these fire ant alkaloids determined via VCD spectroscopy.
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