ArticleAngewandte Chemie (International ed. in English)2021
Catalytic Enantioselective Access to Dihydroquinoxalinones via Formal α-Halo Acyl Halide Synthon in One Pot.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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9 citing papers in PubMed, 24 citations in OpenAlex.
- Domino Strategies in Heterocycle Synthesis: Advancing from Organocatalysis to Photo-/Organo-Autocatalysis.ACS central science · 2026Review
- Serendipity-Driven Telescoped Synthesis of 2-Aryl Glycidic Esters from Aldehydes.Organic letters · 2026Article
- Enantioselective Route to Terminal 2,3-Epoxy Tosylates Enabled by Cooperative Organocatalytic Desymmetrization of 2-Substituted Glycerol Derivatives.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Chiral phosphoric acid-catalyzed asymmetric epoxidation of alkenyl aza-heteroarenes using hydrogen peroxide.Nature communications · 2024Article
- Single-Flask Enantioselective Synthesis of α-Amino Acid Esters by Organocatalysis.Organic letters · 2023Article
- Asymmetric Catalytic Access to Piperazin-2-ones and Morpholin-2-ones in a One-Pot Approach: Rapid Synthesis of an Intermediate to Aprepitant.The Journal of organic chemistry · 2023Article
- Epoxides: Small Rings to Play with under Asymmetric Organocatalysis.ACS organic & inorganic Au · 2022Review
- Supported Gold Nanoparticle-Catalyzed Selective Reduction of Multifunctional, Aromatic Nitro Precursors into Amines and Synthesis of 3,4-Dihydroquinoxalin-2-Ones.Molecules (Basel, Switzerland) · 2022Article
- Catalytic Enantioselective Access to Dihydroquinoxalinones via Formal α-Halo Acyl Halide Synthon in One Pot.Angewandte Chemie (International ed. in English) · 2021Article
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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
An enantioselective one-pot catalytic strategy to dihydroquinoxalinones, featuring novel 1-phenylsulfonyl-1-cyano enantioenriched epoxides as masked α-halo acyl halide synthons, followed by a domino ring-opening cyclization (DROC), is documented. A popular quinine-derived urea served as the catalyst in two out of the three steps performed in the same solvent using commercially available aldehydes, (phenylsulfonyl)acetonitrile, cumyl hydroperoxide and 1,2-phenylendiamines. Medicinally relevant 3-aryl/alkyl-substituted heterocycles are isolated in generally good to high overall yield and high enantioselectivity (up to 99 % ee). A rare example of excellent reusability of an organocatalyst at higher scale, subjected to oxidative conditions, is demonstrated. Mechanistically, labile α-ketosulfone has been detected as the intermediate involved in the DROC process. Theoretical calculations on the key epoxidation step rationalize the observed stereocontrol, highlighting the important role played by the sulfone group.
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