Asymmetric Cu-Catalyzed 1,4-Dearomatization of Pyridines and Pyridazines Without Preactivation of the Heterocycle or Nucleophile

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2018 Apr 4

PMID 29609461

Citations 33

Authors

Michael W Gribble Jr

Sheng Guo

Stephen L Buchwald

Affiliations

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Abstract

We show that a chiral copper hydride (CuH) complex catalyzes C-C bond-forming dearomatization of pyridines and pyridazines at room temperature. The catalytic reaction operates directly on free heterocycles and generates the nucleophiles in situ, eliminating the need for stoichiometric preactivation of either reaction partner; further, it is one of very few methods available for the enantioselective 1,4-dearomatization of heteroarenes. Combining the dearomatization with facile derivatization steps enables one-pot syntheses of enantioenriched pyridines and piperidines.

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