ArticleNature chemistry2024
A directed enolization strategy enables by-product-free construction of contiguous stereocentres en route to complex amino acids.
Article in Nature chemistry, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Umpolung Character of Styrenes: Mechanism and Stereoselective Studies of α, β-Substituted Amino Acids Using Chiral Ir-Phosphine Complexes.Journal of computational chemistry · 2026Article
- Iridium-Catalyzed Stereoselective α-Alkylation of α-Hydroxy Ketones with Minimally Polarized Alkenes.Journal of the American Chemical Society · 2026Article
- β-Substituted Styrenes in Heteroaryl-Directed Hydroalkylative Cross-Couplings: Regio-, Diastereo-, and Enantioselective Formation of β-Stereogenic Tertiary Alcohols.Journal of the American Chemical Society · 2025Article
- Tailored amination enables switchable synthesis of α- and γ-amino acid derivatives from extended quinone methides.Nature communications · 2025Article
- Direct, Asymmetric, and Stereodivergent Reactions ofThe Journal of organic chemistry · 2025Article
- β-Quaternary α-Amino Acids via Iridium-Catalyzed Branched and Enantioselective Hydroalkylation of 1,1-Disubstituted Styrenes.Angewandte Chemie (International ed. in English) · 2025Article
- Dynamic Kinetic Asymmetric Hydroacylation: Racemization by Soft Enolization.Journal of the American Chemical Society · 2025Article
- Heteroaryl-Directed Iridium-Catalyzed Enantioselective C-H Alkenylations of Secondary Alcohols.Journal of the American Chemical Society · 2025Article
- An Aza-Enolate Strategy Enables Iridium-Catalyzed Enantioselective Hydroalkenylations of Minimally Polarized Alkenes en Route to Complex N-Aryl βJournal of the American Chemical Society · 2024Article
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4 authors.
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Abstract
Homochiral α-amino acids are widely used in pharmaceutical design as key subunits in chiral catalyst synthesis or as building blocks in synthetic biology. Many synthetic methods have been developed to access rare or unnatural variants by controlling the installation of the α-stereocentre. By contrast, and despite their importance, α-amino acids possessing β-stereocentres are much harder to synthesize. Here we demonstrate an iridium-catalysed protocol that allows the direct upconversion of simple alkenes and glycine derivatives to give β-substituted α-amino acids with exceptional levels of regio- and stereocontrol. Our method exploits the native directing ability of a glycine-derived N-H unit to facilitate Ir-catalysed enolization of the adjacent carbonyl. The resulting stereodefined enolate cross-couples with a styrene or α-olefin to install two contiguous stereocentres. The process offers very high levels of regio- and stereocontrol and occurs with complete atom economy. In broader terms, our reaction design offers a unique directing-group-controlled strategy for the direct stereocontrolled α-alkylation of carbonyl compounds, and provides a powerful approach for the synthesis of challenging contiguous stereocentres.
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