ArticleAngewandte Chemie (International ed. in English)2018
A Modified System for the Synthesis of Enantioenriched N-Arylamines through Copper-Catalyzed Hydroamination.
Article in Angewandte Chemie (International ed. in English), 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 75 citations in OpenAlex.
- Stereodivergent synthesis of chiral amines bearing vicinal stereocenters via hydroamination of trisubstituted alkenes.Nature communications · 2026Article
- Copper-Catalyzed Stereospecific Transformations of Alkylboronic Esters.Journal of the American Chemical Society · 2022Article
- Design, scope and mechanism of highly active and selective chiral NHC-iridium catalysts for the intramolecular hydroamination of a variety of unactivated aminoalkenes.Chemical science · 2021Article
- CuH-Catalyzed Olefin Functionalization: From Hydroamination to Carbonyl Addition.Accounts of chemical research · 2020Article
- Diastereo- and Enantioselective CuH-Catalyzed Hydroamination of Strained Trisubstituted Alkenes.ACS catalysis · 2020Article
- Cu-Catalyzed Asymmetric Aminoboration ofOrganic letters · 2019Article
- Asymmetric Synthesis of γ-Amino Alcohols by Copper-Catalyzed Hydroamination.Organic letters · 2019Article
- Cross-Coupling of Heteroatomic Electrophiles.Chemical reviews · 2019Review
- Regio- and Enantioselective Synthesis of 1,2-Diamine Derivatives by Copper-Catalyzed Hydroamination.Organic letters · 2019Article
- Preparation of Chiral Allenes through Pd-Catalyzed Intermolecular Hydroamination of Conjugated Enynes: Enantioselective Synthesis Enabled by Catalyst Design.Journal of the American Chemical Society · 2019Article
- Catalytic Asymmetric Synthesis of α-Arylpyrrolidines and Benzo-fused Nitrogen Heterocycles.Angewandte Chemie (International ed. in English) · 2019Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
Despite significant recent progress in copper-catalyzed enantioselective hydroamination chemistry, the synthesis of chiral N-arylamines, which are frequently found in natural products and pharmaceuticals, has not been realized. Initial experiments with N-arylhydroxylamine ester electrophiles were unsuccessful and, instead, their reduction in the presence of copper hydride (CuH) catalysts was observed. Herein, we report key modifications to our previously reported hydroamination methods that lead to broadly applicable conditions for the enantioselective net addition of secondary anilines across the double bond of styrenes, 1,1-disubstituted olefins, and terminal alkenes. NMR studies suggest that suppression of the undesired reduction pathway is the basis for the dramatic improvements in yield under the reported method.
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