Synfacts 2018; 14(07): 0707
DOI: 10.1055/s-0037-1609533
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Dearomatization of Pyridines with Styrene-Derived Nucleophiles

Mark Lautens
Andrew Whyte
Gribble Jr MW. Guo S. Buchwald SL. * Massachusetts Institute of Technology, Cambridge, USA
Asymmetric Cu-Catalyzed 1,4-Dearomatization of Pyridines and Pyridazines without Preactivation of the Heterocycle or Nucleophile.

J. Am. Chem. Soc. 2018;
140: 5057-5060
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18. Juni 2018 (online)



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.



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.