ArticleChemistry (Weinheim an der Bergstrasse, Germany)2020
Prebiotically Plausible Organocatalysts Enabling a Selective Photoredox α-Alkylation of Aldehydes on the Early Earth.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed, 22 citations in OpenAlex.
- Organocatalyzed bottom-up formation of protocells.Nature communications · 2026Article
- Dual-Mode Thio-MacMillan Organocatalysts: Stereoselective Diels-Alder Reactions or Sacrificial Self-Cyclization to N-Bridged Bicyclic Lactams.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Why pyridoxal phosphate could be a functional predecessor of thiamine pyrophosphate and speculations on a primordial metabolism.RSC chemical biology · 2024Review
- Nucleophilicity of 4-(Alkylthio)-3-imidazoline Derived Enamines.Chemistry (Weinheim an der Bergstrasse, Germany) · 2024Article
- Biocompatible α-Methylenation of Metabolic Butyraldehyde in Living Bacteria.Angewandte Chemie (International ed. in English) · 2023Article
- The effect ofChemical communications (Cambridge, England) · 2023Article
- Dynamic Exchange of Substituents in a Prebiotic Organocatalyst: Initial Steps towards an Evolutionary System.Angewandte Chemie (International ed. in English) · 2022Article
- Prebiotically Plausible Organocatalysts Enabling a Selective Photoredox α-Alkylation of Aldehydes on the Early Earth.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
Corrections and comments
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Authors and funding
4 authors at 2 institutions in 1 country.
Funding
Abstract
Organocatalysis is a powerful approach to extend and (enantio-) selectively modify molecular structures. Adapting this concept to the Early Earth scenario offers a promising solution to explain their evolution into a complex homochiral world. Herein, we present a class of imidazolidine-4-thione organocatalysts, easily accessible from simple molecules available on an Early Earth under highly plausible prebiotic reaction conditions. These imidazolidine-4-thiones are readily formed from mixtures of aldehydes or ketones in presence of ammonia, cyanides and hydrogen sulfide in high selectivity and distinct preference for individual compounds of the resulting catalyst library. These organocatalysts enable the enantioselective α-alkylation of aldehydes under prebiotic conditions and show activities that correlate with the selectivity of their formation. Furthermore, the crystallization of single catalysts as conglomerates opens the pathway for symmetry breaking.
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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.