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. 2016 Feb 5;55(6):2205-9.
doi: 10.1002/anie.201510027. Epub 2015 Dec 22.

Synthesis and Utility of Dihydropyridine Boronic Esters

Santanu Panda  1 , Aaron Coffin  1 , Q Nhu Nguyen  2 , Dean J Tantillo  2 , Joseph M Ready  3
Affiliations

Synthesis and Utility of Dihydropyridine Boronic Esters

Santanu Panda et al. Angew Chem Int Ed Engl. .

Abstract

When activated by an acylating agent, pyridine boronic esters react with organometallic reagents to form a dihydropyridine boronic ester. This intermediate allows access to a number of valuable substituted pyridine, dihydropyridine, and piperidine products.

Keywords: allylic compounds; boron; heterocycles; samarium iodide; synthetic methods.

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Figures

Scheme 1
Scheme 1
Selected functionalization of pyridines.
Scheme 2
Scheme 2
Generation of dihydropyridines.
Scheme 3
Scheme 3
Functionalization of Dihydropyridine Intermediates. [a]nBuLi (1 equiv.), BzCI (1.1 equiv); then PhCHO (4 equiv.)
Scheme 4
Scheme 4
Cyclization of dihydropyridines with SmI2. DIBAL = iBu2AIH.
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