ArticleAngewandte Chemie (International ed. in English)2020
Photochemically Induced Ring Opening of Spirocyclopropyl Oxindoles: Evidence for a Triplet 1,3-Diradical Intermediate and Deracemization by a Chiral Sensitizer.
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 21 papers.
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Who cites it
21 citing papers in PubMed.
- Photochemical Deracemization of Aza-1-isoindolinones: Critical Influence of Catalyst Substitution and the Nature of Its Resting State.Journal of the American Chemical Society · 2026Article
- Bifunctional Photocatalysts: Exploiting Proximity for Enhanced Reaction Performance.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Review
- 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
- Bicyclo[1.1.0]tetragermane-2,4-diide Diradicaloid.Angewandte Chemie (International ed. in English) · 2025Article
- Privileged Chiral Photocatalysts.Angewandte Chemie (International ed. in English) · 2025Review
- Oxetane Cleavage Pathways in the Excited State: Photochemical Kinetic Resolution as an Approach to Enantiopure Oxetanes.Journal of the American Chemical Society · 2025Article
- Asymmetric photoreactions catalyzed by chiral ketones.RSC advances · 2025Review
- Photochemical Deracemization of 4,7-Diaza-1-isoindolinones by Unidirectional Hydrogen Atom Shuttling.Journal of the American Chemical Society · 2025Article
- Article
- Light-driven redox deracemization of indolines and tetrahydroquinolines using a photocatalyst coupled with chiral phosphoric acid.Chemical science · 2023Article
- Photocatalytic deracemisation of cobalt(III) complexes with fourfold stereogenicity.Chemical communications (Cambridge, England) · 2022Article
- Energy transfer (EnT) photocatalysis enabled by gold-N-heterocyclic carbene (NHC) complexes.Chemical science · 2022Article
- Mechanistic insights into photochemical nickel-catalyzed cross-couplings enabled by energy transfer.Nature communications · 2022Article
- 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
- Photo-Induced Ruthenium-Catalyzed C-H Benzylations and Allylations at Room Temperature.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Visible-Light-Driven Catalytic Deracemization of Secondary Alcohols.Angewandte Chemie (International ed. in English) · 2021Article
- Fluorescence-Detected Pump-Probe Spectroscopy.Angewandte Chemie (International ed. in English) · 2021Article
- Enantioselective, Visible Light Mediated Aza Paternò-Büchi Reactions of Quinoxalinones.Angewandte Chemie (International ed. in English) · 2021Article
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6 authors.
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Abstract
The photochemical deracemization of spiro[cyclopropane-1,3'-indolin]-2'-ones (spirocyclopropyl oxindoles) was studied. The corresponding 2,2-dichloro compound is configurationally labile upon direct irradiation at λ=350 nm and upon irradiation at λ=405 nm in the presence of achiral thioxanthen-9-one as the sensitizer. The triplet 1,3-diradical intermediate generated in the latter reaction was detected by transient absorption spectroscopy and its lifetime determined (τ=22 μs). Using a chiral thioxanthone or xanthone, with a lactam hydrogen bonding site as a photosensitizer, allowed the deracemization of differently substituted chiral spirocyclopropyl oxindoles with yields of 65-98 % and in 50-85 % ee (17 examples). Three mechanistic contributions were identified to co-act favorably for high enantioselectivity: the difference in binding constants to the chiral thioxanthone, the smaller molecular distance in the complex of the minor enantiomer, and the lifetime of the intermediate 1,3-diradical.
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