ArticleJournal of the American Chemical Society2017
Tandem Palladium and Isothiourea Relay Catalysis: Enantioselective Synthesis of α-Amino Acid Derivatives via Allylic Amination and [2,3]-Sigmatropic Rearrangement.
Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 38 papers.
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Who cites it
38 citing papers in PubMed, 125 citations in OpenAlex.
- The Catalytic Enantioselective Sommelet-Hauser Rearrangement.Journal of the American Chemical Society · 2026Article
- A promising dual catalytic "Isothiourea + X" platform: from classic ionic to radical transformations.RSC advances · 2026Review
- Isochalcogenourea-catalyzed asymmetric (4 + 2)-heterocycloadditions of allenoates.Chemistry letters · 2024Article
- Tandem catalytic allylic C-H amination and asymmetric [2,3]-rearrangementChemical science · 2024Article
- Difluorocarbene-induced [1,2]- and [2,3]-Stevens rearrangement of tertiary amines.Nature communications · 2024Article
- Organophosphates as Versatile Substrates in Organic Synthesis.Molecules (Basel, Switzerland) · 2024Review
- Enantioselective α-heterofunctionalization reactions of catalytically generated C1-Lewis base enolates.Tetrahedron chem · 2024Article
- Friedel-CraftsACS organic & inorganic Au · 2024Article
- Catalytic stereodivergent allylic alkylation of 2-acylimidazoles for natural product synthesis.Nature communications · 2023Article
- Cooperative Chiral Lewis Base/Palladium-Catalyzed Asymmetric Syntheses of Methylene-Containing δ-Lactams.European journal of organic chemistry · 2023Article
- Enantioselective isothiourea-catalysed reversible Michael addition of aryl esters to 2-benzylidene malononitriles.Chemical science · 2023Article
- The Synthesis and Biological Evaluation of 2-(1Molecules (Basel, Switzerland) · 2023Article
- Silver/chiral pyrrolidinopyridine relay catalytic cycloisomerization/(2 + 3) cycloadditions of enynamides to asymmetrically synthesize bispirocyclopentenes as PDE1B inhibitors.Communications chemistry · 2023Article
- Recent advances in metal-catalysed asymmetric sigmatropic rearrangements.Chemical science · 2022Review
- Sigmatropic [1,5] Carbon Shift of Transient C3 Ammonium Enolates.Angewandte Chemie (International ed. in English) · 2022Article
- Cooperative Palladium/Isothiourea Catalyzed Enantioselective Formal (3+2) Cycloaddition of Vinylcyclopropanes and α,β-Unsaturated Esters.Angewandte Chemie (International ed. in English) · 2022Article
- Solvent directed chemically divergent synthesis of β-lactams and α-amino acid derivatives with chiral isothiourea.Chemical science · 2022Article
- Synthesis of Enantioenriched 3,4-Disubstituted Chromans through Lewis Base Catalyzed Carbosulfenylation.The Journal of organic chemistry · 2021Article
- Isothiourea-Catalyzed Enantioselective α-Alkylation of Esters via 1,6-Conjugate Addition toMolecules (Basel, Switzerland) · 2021Article
- Catalytic enantioselective synthesis of 1,4-dihydropyridinesChemical science · 2021Article
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
A tandem relay catalytic protocol using both Pd and isothiourea catalysis has been developed for the enantioselective synthesis of α-amino acid derivatives containing two stereogenic centers from readily accessible N,N-disubstituted glycine aryl esters and allylic phosphates. The optimized process uses a bench-stable succinimide-based Pd precatalyst (FurCat) to promote Pd-catalyzed allylic ammonium salt generation from the allylic phosphate and the glycine aryl ester. Subsequent in situ enantioselective [2,3]-sigmatropic rearrangement catalyzed by the isothiourea benzotetramisole forms syn-α-amino acid derivatives with high diastereo- and enantioselectivity. This methodology is most effective using 4-nitrophenylglycine esters and tolerates a variety of substituted cinnamic and styrenyl allylic ethyl phosphates. The use of challenging unsymmetrical N-allyl-N-methylglycine esters is also tolerated under the catalytic relay conditions without compromising stereoselectivity.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.