ArticleJournal of the American Chemical Society2021
Asymmetric Synthesis of Protected Unnatural α-Amino Acids via Enantioconvergent Nickel-Catalyzed Cross-Coupling.
Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed.
- Kinetic resolution of amino acids by phosphine oxide catalyzed enantioselective esterification.Nature communications · 2026Article
- Modular assembly of chiral amino acid derivatives and peptides from commonly available feedstocks.Nature communications · 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
- Molybdenum-Catalyzed Asymmetric Amination of α-Hydroxy Esters: Synthesis of α-Amino Acids.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- Biocatalytic Synthesis of α-Amino Esters via Nitrene C-H Insertion.Journal of the American Chemical Society · 2024Article
- A directed enolization strategy enables by-product-free construction of contiguous stereocentres en route to complex amino acids.Nature chemistry · 2024Article
- Article
- Modular α-tertiary amino ester synthesis through cobalt-catalysed asymmetric aza-Barbier reaction.Nature chemistry · 2024Article
- Metal-Catalyzed Enantioconvergent Transformations.Chemical reviews · 2023Review
- Enantioselective Csp3-Csp3 formation by nickel-catalyzed enantioconvergent cross-electrophile alkyl-alkyl coupling of unactivated alkyl halides.Science advances · 2023Article
- Synthesis of Bis(amino acids) Containing the Styryl-cyclobutane Core by Photosensitized [2+2]-Cross-cycloaddition of Allylidene-5(4International journal of molecular sciences · 2023Article
- Modular Synthesis of Unnatural Peptides via Rh(III)-Catalyzed Diastereoselective Three-Component Carboamidation Reaction.Journal of the American Chemical Society · 2023Article
- A Vitamin BAngewandte Chemie (International ed. in English) · 2022Article
- A Vitamin BAngewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2022Article
- Late-Stage Modification of Oligopeptides by Nickel-Catalyzed Stereoselective Radical Addition to Dehydroalanine.Angewandte Chemie (International ed. in English) · 2022Article
- Article
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3 authors.
Funding
Abstract
Interest in unnatural α-amino acids has increased rapidly in recent years in areas ranging from protein design to medicinal chemistry to materials science. Consequently, the development of efficient, versatile, and straightforward methods for their enantioselective synthesis is an important objective in reaction development. In this report, we establish that a chiral catalyst based on nickel, an earth-abundant metal, can achieve the enantioconvergent coupling of readily available racemic alkyl electrophiles with a wide variety of alkylzinc reagents (1:1.1 ratio) to afford protected unnatural α-amino acids in good yield and ee. This cross-coupling, which proceeds under mild conditions and is tolerant of air, moisture, and a broad array of functional groups, complements earlier approaches to the catalytic asymmetric synthesis of this valuable family of molecules. We have applied our new method to the generation of several enantioenriched unnatural α-amino acids that have previously been shown to serve as useful intermediates in the synthesis of bioactive compounds.
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