Enantioselective Dearomatization of Pyridines with Styrene-Derived Nucleophiles

Key words

copper catalysis - dearomatization - pyridines

Significance

Dearomatization of heteroaromatics is a valuable transformation in organic chemistry to create new carbon–carbon bonds. Herein, Buchwald and co-workers report the dearomatization of pyridines with a chiral benzylic copper species generated through an enantioselective copper hydride addition to the corresponding ­styrene.

 

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Comment

The intermediate dihydropyridine could be oxidized to regenerate the pyridine or ­reduced to give the piperidine scaffold. A variety of substituents could be tolerated on either the styrene or pyridine, including halogens and alkyl or alkynyl groups. The alkene could also be a β-substituted styrene containing a heteroatom in the ­alkyl chain.

 

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