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CuH-Catalyzed Asymmetric Reductive Amidation of α,β-Unsaturated Carboxylic Acids

Achim Link, Yujing Zhou and Stephen L. Buchwald*

*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States, Email: sbuchwalmit.edu

A. Link, Y. Zhou, S. L. Buchwald, Org. Lett., 2020, 22, 5666-5670.

DOI: 10.1021/acs.orglett.0c02064 (free Supporting Information)


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Abstract

A direct enantioselective copper hydride (CuH)-catalyzed synthesis of β-chiral amides from α,β-unsaturated carboxylic acids and secondary amines under mild reaction conditions tolerates a variety of functional groups in the β-position including several heteroarenes. A subsequent iridium-catalyzed reduction to γ-chiral amines can be performed in the same flask.

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Key Words

1,4-reduction of α,β-unsaturated compounds, amides, dimethoxymethylsilane


ID: J54-Y2020