ArticleJournal of the American Chemical Society2022
Asymmetric Photochemical [2 + 2]-Cycloaddition of Acyclic Vinylpyridines through Ternary Complex Formation and an Uncontrolled Sensitization Mechanism.
Article in Journal of the American Chemical Society, 2022. 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.
- Excitation of acyclic trisubstituted alkenes via triplet energy transfer for diastereo- and enantioselective [2 + 2] photocycloaddition.Nature communications · 2026Article
- Visible-Light-Mediated Lewis Acid-Catalyzed Diradical Hydrogen Atom Transfer Reaction of Enamides.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Decoding skeletal diversity and complexity: A biomimetic and photochemical remodeling strategy.Science advances · 2026Article
- Synthesis of aryl-fused bicyclo[3.1.1]heptanes and validation as naphthyl bioisosteres.Nature chemistry · 2026Article
- Photochemical deracemization of 2,3-allenoic acids mediated by a sensitizing chiral phosphoric acid catalyst.Chemical science · 2025Article
- Enantioselective Photochemical Generation of a Short-Lived, Twisted Cycloheptenone Isomer: Catalytic Formation, Detection, and Consecutive Chemistry.Angewandte Chemie (International ed. in English) · 2025Article
- Counterion Effects in [Ru(bpy)JACS Au · 2024Article
- Catalytic asymmetric [4 + 2] dearomative photocycloadditions of anthracene and its derivatives with alkenylazaarenes.Nature communications · 2024Article
Corrections and comments
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Authors and funding
7 authors.
Funding
Abstract
Stereochemical control of photochemical reactions that occur via triplet energy transfer remains a challenge. Suppressing off-catalyst stereorandom reactivity is difficult for highly reactive open-shell intermediates. Strategies for suppressing racemate-producing, off-catalyst pathways have long focused on formation of ground state, substrate-catalyst chiral complexes that are primed for triplet energy transfer via a photocatalyst in contrast to their off-catalyst counterparts. Herein, we describe a strategy where both a chiral catalyst-associated vinylpyridine and a nonassociated, free vinylpyridine substrate can be sensitized by an Ir(III) photocatalyst, yet high levels of diastereo- and enantioselectivity in a [2 + 2] photocycloaddition are achieved through a preferred, highly organized transition state. This mechanistic paradigm is distinct from, yet complementary to current approaches for achieving high levels of stereocontrol in photochemical transformations.
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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.