Redox cycloisomerization approach to 1,2-dihydropyridines

Organic Letters
Barry M Trost, Berenger Biannic

Abstract

The phosphine-catalyzed synthesis of 1,2-dihydropyridines via an alkyne isomerization/electrocyclization sequence is described. Propargylidenecarbamate substrates were prepared following a one-pot procedure between a terminal alkyne, a benzonitrile, and a chloroformate in the presence of trimethylaluminum. This methodology gives access to a diverse set of 2,6-disubstituted 1,2-dihydropyridines in high yield. The products can be easily converted into substituted piperidines or pyridines, and this methodology was applied to the synthesis of indolizidines.

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Citations

Jan 7, 2017·Chemical Science·J Patrick LutzAbigail G Doyle
Jun 2, 2020·Organic & Biomolecular Chemistry·Nikhil SrivastavaHyun-Joon Ha

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