ArticleChemical science2017
Anion-π catalysis: bicyclic products with four contiguous stereogenic centers from otherwise elusive diastereospecific domino reactions on π-acidic surfaces.
Article in Chemical science, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed, 39 citations in OpenAlex.
- Anion-π Catalysis Enabled by the Mechanical Bond.Angewandte Chemie (International ed. in English) · 2022Article
- The role of streptavidin and its variants in catalysis by biotinylated secondary amines.Organic & biomolecular chemistry · 2021Article
- Enabling protein-hosted organocatalytic transformations.RSC advances · 2020Review
- Article
- Reactivity and Selectivity of Iminium Organocatalysis Improved by a Protein Host.Angewandte Chemie (International ed. in English) · 2018Article
- Carbon-Halogen Bond Activation by Selenium-Based Chalcogen Bonding.Angewandte Chemie (International ed. in English) · 2017Article
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Authors and funding
6 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Anion-π interactions have been introduced recently to catalysis. The idea of stabilizing anionic intermediates and transition states on π-acidic surfaces is a new fundamental concept. By now, examples exist for asymmetric enolate, enamine, iminium and transamination chemistry, and the first anion-π enzyme has been created. Delocalized over large aromatic planes, anion-π interactions appear particularly attractive to stabilize extensive long-distance charge displacements during domino processes. Moving on from the formation of cyclohexane rings with five stereogenic centers in one step on a π-acidic surface, we here focus on asymmetric anion-π catalysis of domino reactions that afford bicyclic products with quaternary stereogenic centers. Catalyst screening includes a newly synthesized, better performing anion-π version of classical organocatalysts from cinchona alkaloids, and anion-π enzymes. We find stereoselectivities that are clearly better than the best ones reported with conventional catalysts, culminating in unprecedented diastereospecificity. Moreover, we describe achiral salts as supramolecular chirality enhancers and report the first artificial enzyme that operates in neutral water with anion-π interactions,
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Registered trials
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