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. 2015 Mar 20;17(6):1433-6.
doi: 10.1021/acs.orglett.5b00279. Epub 2015 Mar 11.

Redox cycloisomerization approach to 1,2-dihydropyridines

Barry M Trost  1 , Berenger Biannic  1
Affiliations

Redox cycloisomerization approach to 1,2-dihydropyridines

Barry M Trost et al. Org Lett. .

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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Figures

Scheme 1
Scheme 1
Phosphine-Catalyzed Isomerization of Alkynes to 1,3-Diene
Scheme 2
Scheme 2
One-Pot Substrate Synthesis
Scheme 3
Scheme 3
Product Scope
Scheme 4
Scheme 4
Synthetic Applications
Scheme 5
Scheme 5
Concise Synthesis of Indolizidine 39
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