Silver Ion-Induced Grob Fragmentation of γ-Amino Iodides: Highly Stereoselective Synthesis of Polysubstituted Piperidines

A new concerted silver ion-mediated Grob fragmentation process is described in which a 1,2-dihydropyridinium ion is formed and trapped in situ with Grignard reagents in a highly regio- and diastereoselective fashion. Using this methodology, 2,3,6-trisubstituted piperidines were synthesized in good y...

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Veröffentlicht in:	Organic letters 2008-12, Vol.10 (23), p.5497-5499
Hauptverfasser:	Barbe, Guillaume, St-Onge, Miguel, Charette, André B
Format:	Artikel
Sprache:	eng
Schlagworte:	Iodides - chemistry Piperidines - chemical synthesis Piperidines - chemistry Silver - chemistry Stereoisomerism Substrate Specificity
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creator	Barbe, Guillaume St-Onge, Miguel Charette, André B
description	A new concerted silver ion-mediated Grob fragmentation process is described in which a 1,2-dihydropyridinium ion is formed and trapped in situ with Grignard reagents in a highly regio- and diastereoselective fashion. Using this methodology, 2,3,6-trisubstituted piperidines were synthesized in good yields and further derivatized to polysubstituted indolizidine.
doi_str_mv	10.1021/ol8024605
format	Article
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subjects	Iodides - chemistry Piperidines - chemical synthesis Piperidines - chemistry Silver - chemistry Stereoisomerism Substrate Specificity
title	Silver Ion-Induced Grob Fragmentation of γ-Amino Iodides: Highly Stereoselective Synthesis of Polysubstituted Piperidines
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