ArticleAngewandte Chemie (International ed. in English)2020
Photochemical Deracemization of Allenes and Subsequent Chirality Transfer.
Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed, 93 citations in OpenAlex.
- Bifunctional Photocatalysts: Exploiting Proximity for Enhanced Reaction Performance.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Review
- Unlocking enzymatic deracemization of structurally diverse allenes by designed photoenzymes.Nature communications · 2026Article
- Catalytic Deracemization of 1,2-Aminoalcohols through Enantioselective Hydrogen Atom Abstraction.Journal of the American Chemical Society · 2026Article
- Construction of sulfur stereocentres by asymmetric geminate recasting.Nature chemistry · 2025Article
- Visible-Light Mediated Activation of 1,3-Dienes and Allenes via Energy Transfers.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Photochemical deracemization of 2,3-allenoic acids mediated by a sensitizing chiral phosphoric acid catalyst.Chemical science · 2025Article
- Privileged Chiral Photocatalysts.Angewandte Chemie (International ed. in English) · 2025Review
- Asymmetric photoreactions catalyzed by chiral ketones.RSC advances · 2025Review
- Construction of axially chiral molecules enabled by photoinduced enantioselective reactions.Chemical science · 2024Review
- Tandem Isomerization/α,β-Site-Selective and Enantioselective Addition Reactions ofJournal of the American Chemical Society · 2023Article
- Intermolecular dearomative [4 + 2] cycloaddition of naphthalenesChemical science · 2022Article
- Synergistic Strategies in Aminocatalysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Review
- Transition Metal Catalysis Controlled by Hydrogen Bonding in the Second Coordination Sphere.Chemical reviews · 2022Review
- Reactivity and selectivity modulation within a molecular assembly: recent examples from photochemistry.Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology · 2022Review
- Chiral Photocatalyst Structures in Asymmetric Photochemical Synthesis.Chemical reviews · 2022Review
- Visible-Light-Driven Catalytic Deracemization of Secondary Alcohols.Angewandte Chemie (International ed. in English) · 2021Article
- Enantioselective, Visible Light Mediated Aza Paternò-Büchi Reactions of Quinoxalinones.Angewandte Chemie (International ed. in English) · 2021Article
- Photochemically Induced Ring Opening of Spirocyclopropyl Oxindoles: Evidence for a Triplet 1,3-Diradical Intermediate and Deracemization by a Chiral Sensitizer.Angewandte Chemie (International ed. in English) · 2020Article
- Photochemical Deracemization of Allenes and Subsequent Chirality Transfer.Angewandte Chemie (International ed. in English) · 2020Article
- Recent developments in enantioselective photocatalysis.Beilstein journal of organic chemistry · 2020Review
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Trisubstituted allenes with a 3-(1'-alkenylidene)-pyrrolidin-2-one motif were successfully deracemized (13 examples, 86-98 % ee) employing visible light (λ=420 nm) and a chiral triplet sensitizer as the catalyst (2.5 mol %). The photocatalyst likely operates by selective recognition of one allene enantiomer via hydrogen bonds and by a triplet-sensitized racemization process. Even a tetrasubstituted allene (45 % ee) and a seven-membered 3-(1'-alkenylidene)-azepan-2-one (62 % ee) could be enantiomerically enriched under the chosen conditions. It was shown that the axial chirality of the allenes can be converted into point chirality by a Diels-Alder (94-97 % ee) or a bromination reaction (91 % ee). Ring opening of the five-membered pyrrolidin-2-one was achieved without significantly compromising the integrity of the chirality axis (92 % ee).
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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.