ArticleJournal of the American Chemical Society2024
Asymmetric Synthesis of α-Chloroamides via Photoenzymatic Hydroalkylation of Olefins.
Article in Journal of the American Chemical Society, 2024. 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.
- Machine-Learning-Enabled Rapid Evolution of Photoenzymes for the Asymmetric Synthesis of gem-Difluorophosphonates.Angewandte Chemie (International ed. in English) · 2026Article
- Asymmetric synthesis of alkyl fluoridesGreen chemistry : an international journal and green chemistry resource : GC · 2026Article
- Designing and Engineering Enzymes for New-to-Nature Photobiocatalysis.Methods in molecular biology (Clifton, N.J.) · 2026Review
- Aromatic Coupling Reactions Catalyzed by "ene"-Reductase under Visible Light Irradiation.ACS omega · 2025Article
- Is a Malleable Active Site Loop the Key to High Substrate Promiscuity? Hybrid, Biocatalytic Route to Structurally Diverse Taxoid Side Chains with Remarkable Dual Stereocontrol.Angewandte Chemie (International ed. in English) · 2025Article
- Enantioconvergent Cobalt-Catalyzed Hydroalkylation for the Construction of Fluoro, Chloro, and Trifluoromethyl Stereogenic Centers.Angewandte Chemie (International ed. in English) · 2025Article
- Photoenzymatic enantioselective synthesis of fluorinated amides with remote stereocenter.Nature communications · 2025Article
- Machine Learning Guided Rational Design of a Non-Heme Iron-Based Lysine Dioxygenase Improves its Total Turnover Number.Chembiochem : a European journal of chemical biology · 2024Article
- Threonine Aldolase-Catalyzed Enantioselective α-Alkylation of Amino Acids through Unconventional Photoinduced Radical Initiation.Journal of the American Chemical Society · 2024Article
- Stability Oracle: a structure-based graph-transformer framework for identifying stabilizing mutations.Nature communications · 2024Article
- Review
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Authors and funding
8 authors.
Funding
Abstract
Photoenzymatic intermolecular hydroalkylations of olefins are highly enantioselective for chiral centers formed during radical termination but poorly selective for centers set in the C-C bond-forming event. Here, we report the evolution of a flavin-dependent "ene"-reductase to catalyze the coupling of α,α-dichloroamides with alkenes to afford α-chloroamides in good yield with excellent chemo- and stereoselectivity. These products can serve as linchpins in the synthesis of pharmaceutically valuable motifs. Mechanistic studies indicate that radical formation occurs by exciting a charge-transfer complex templated by the protein. Precise control over the orientation of molecules within the charge-transfer complex potentially accounts for the observed stereoselectivity. The work expands the types of motifs that can be prepared using photoenzymatic catalysis.
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