ArticleNature chemistry2012
Combinatorial evolution of site- and enantioselective catalysts for polyene epoxidation.
Article in Nature chemistry, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 49 papers.
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Who cites it
49 citing papers in PubMed.
- Harnessing Random Polymers as Chemoselective Catalysts With Structural Adaptability: Epoxidation of Olefinic Quaternary Ammonium Salts via Charge Recognition.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Selective Oxidation of Disparate Functional Groups Mediated by a Common Aspartic Acid-Based Peptide Catalyst Platform.Accounts of chemical research · 2025Article
- Engineering and Exploiting Immobilized Peptide Organocatalysts for Modern Synthesis.Molecules (Basel, Switzerland) · 2025Review
- Palladium-Catalyzed Site-Selective Regiodivergent Carbocyclization of Di- and Trienallenes: A Switch between Substituted Cyclohexene and Cyclobutene.Journal of the American Chemical Society · 2025Article
- Conformational Analysis and Organocatalytic Activity of Helical Stapled Peptides Containing α-Carbocyclic α,α-Disubstituted α-Amino Acids.Molecules (Basel, Switzerland) · 2024Article
- Organocatalytic activation of hydrogen peroxide: towards green and sustainable oxidations.Chemical science · 2024Review
- Site-selective chemical reactions by on-water surface sequential assembly.Nature communications · 2023Article
- Aspartyl β-Turn-Based Dirhodium(II) Metallopeptides for Benzylic C(spJournal of the American Chemical Society · 2023Article
- Generality-oriented optimization of enantioselective aminoxyl radical catalysis.Science (New York, N.Y.) · 2023Article
- Investigation of the Effect of Turn Residues on Tetrapeptide Aldol Catalysts with β-Turn Propensity.ACS omega · 2022Article
- Site-Selective C-H Arylation of Diverse Arenes Ortho to Small Alkyl Groups.Angewandte Chemie (International ed. in English) · 2022Article
- Controlling the Site Selectivity in Acylations of Amphiphilic Diols: Directing the Reaction toward the Apolar Domain in a Model Diol and the Midecamycin AThe Journal of organic chemistry · 2022Article
- Late-Stage Chemoenzymatic Installation of Hydroxy-Bearing Allyl Moiety on the Indole Ring of Tryptophan-Containing Peptides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Site-Selective Catalytic Epoxidation of Alkene with Tunable, Atomic Precision by Molecularly Imprinted Artificial Epoxidases.ACS catalysis · 2022Article
- Site- and Enantioselective Iridium-Catalyzed Desymmetric Mono-Hydrogenation of 1,4-Dienes.Angewandte Chemie (International ed. in English) · 2021Article
- Aldehyde-catalyzed epoxidation of unactivated alkenes with aqueous hydrogen peroxide.Chemical science · 2021Article
- Catalytic Enantioselective Synthesis of Pyridyl Sulfoximines.Journal of the American Chemical Society · 2021Article
- Site-switchable mono-O-allylation of polyols.Nature communications · 2020Article
- Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms.Chemical reviews · 2020Review
- Synergistic photoredox and copper catalysis by diode-like coordination polymer with twisted and polar copper-dye conjugation.Nature communications · 2020Article
Corrections and comments
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2 authors.
Funding
Abstract
Selectivity in the catalytic functionalization of complex molecules is a major challenge in chemical synthesis. The problem is magnified when there are several possible stereochemical outcomes and when similar functional groups occur repeatedly within the same molecule. Selective polyene oxidation provides an archetypical example of this challenge. Historically, enzymatic catalysis has provided the only precedents. Although non-enzymatic catalysts that meet some of these challenges became known, a comprehensive solution has remained elusive. Here, we describe low molecular weight peptide-based catalysts, discovered through a combinatorial synthesis and screening protocol, that exhibit site- and enantioselective oxidation of certain positions of various isoprenols. This diversity-based approach, which exhibits features reminiscent of the directed evolution of enzymes, delivers catalysts that compare favourably to the state-of-the-art for the asymmetric oxidation of these compounds. Moreover, the approach culminated in catalysts that exhibit alternative-site selectivity in comparison to oxidation catalysts previously described.
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