ArticleACS catalysis2020
Diastereo- and Enantioselective CuH-Catalyzed Hydroamination of Strained Trisubstituted Alkenes.
Article in ACS catalysis, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Pathway-divergent coupling of alkynes and cyclobutenes through enantioselective cobalt catalysis.Nature communications · 2025Article
- Copper-Catalyzed Hydroamination: Enantioselective Addition of Pyrazoles to Cyclopropenes.Journal of the American Chemical Society · 2023Article
- Progression of Hydroamination Catalyzed by Late Transition-Metal Complexes from Activated to Unactivated Alkenes.Accounts of chemical research · 2023Article
- Rhodium-Catalyzed Asymmetric Arylation of Cyclobutenone Ketals.Angewandte Chemie (International ed. in English) · 2023Article
- Catalytic asymmetric hydrometallation of cyclobutenes with salicylaldehydes.Chemical science · 2021Article
- A catalytic asymmetric cross-coupling approach to the synthesis of cyclobutanes.Nature chemistry · 2021Article
- Photocatalytic Generation of Aminium Radical Cations for C─N Bond Formation.ACS catalysis · 2020Article
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4 authors.
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Abstract
Amine-substituted cyclobutanes and cyclopropanes are important substructures in biologically active compounds. Moreover, many of the cycloalkane units bear multiple substituents and stereocenters. Therefore, synthetic methods that produce polysubstituted aminocyclobutanes and aminocyclopropanes in a highly diastereo- and enantioselective manner are of importance. Herein, we describe the diastereo- and enantioselective synthesis of various types of polysubstituted aminocyclobutanes and aminocyclopropanes through CuH-catalyzed hydroamination of 1-substituted cyclobutenes and cyclopropenes. These strained trisubstituted alkenes exhibit much higher reactivity compared to their unstrained analogues in the initial hydrocupration step of the reaction. Moreover, an interesting reversal of regioselectivity was observed in the hydroamination of 1-aryl-substituted cyclobutenes compared to the cyclopropene analogues. The origins of the enhanced reactivity of strained trisubstituted alkenes as well as the differences in the regio- and enantioselectivity between reactions with cyclobutenes and cyclopropenes were investigated computationally.
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