ArticleJournal of the American Chemical Society2015
Enantioconvergent synthesis of functionalized γ-butyrolactones via (3 + 2)-annulation.
Article in Journal of the American Chemical Society, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- Innovative Arylimidazole-Fused Phytovirucides via Carbene-Catalyzed [3+4] Cycloaddition: Locking Viral Cell-To-Cell Movement by Out-Competing Virus Capsid-Host Interactions.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Total Synthesis of Polysubstituted γ-Butyrolactone Lignans (-)-Hinokinin, (-)-Bicubebin B, and (-)-Isodeoxypodophyllotoxin via Oxime Carbonate Formation.Organic letters · 2023Article
- Dynamic kinetic resolution of γ,γ-disubstituted indole 2-carboxaldehydesChemical science · 2022Article
- A Review of the Pharmacological Activities and Recent Synthetic Advances of γ-Butyrolactones.International journal of molecular sciences · 2021Review
- New Developments of the Principle of Vinylogy as Applied to π-Extended Enolate-Type Donor Systems.Chemical reviews · 2020Article
- A Cooperative Ternary Catalysis System for Asymmetric Lactonizations of α-Ketoesters.Advanced synthesis & catalysis · 2017Article
- Synthesis of Complex Glycolates by Enantioconvergent Addition Reactions.Accounts of chemical research · 2017Article
- Direct Zinc(II)-Catalyzed Enantioconvergent Additions of Terminal Alkynes to α-Keto Esters.Angewandte Chemie (International ed. in English) · 2017Article
- Palladium-Catalyzed β-Arylation of α-Keto Esters.Organic letters · 2017Article
- Synthesis of Complex Tertiary Glycolates by Enantioconvergent Arylation of Stereochemically Labile α-Keto Esters.Journal of the American Chemical Society · 2017Article
- Diastereoselective Organocatalytic Addition of α-Angelica Lactone to β-Halo-α-ketoesters.The Journal of organic chemistry · 2017Article
- Asymmetric Synthesis of γ-Lactones through Koga Amine-Controlled Addition of Enediolates to α,β-Unsaturated Sulfoxonium Salts.The Journal of organic chemistry · 2017Article
- Asymmetric Synthesis of β-Amino Amides by Catalytic Enantioconvergent 2-Aza-Cope Rearrangement.Journal of the American Chemical Society · 2015Article
- Enantioselective reductive multicomponent coupling reactions between isatins and aldehydes.Chemical science · 2015Article
Corrections and comments
- Erratum issued
Authors and funding
3 authors.
Funding
Abstract
A dynamic kinetic resolution of β-halo α-keto esters in an asymmetric homoenolate reaction is described. A chiral N-hetereocyclic carbene catalyzes the a(3) → d(3)-umpolung addition of α,β-enals to racemic α-keto esters, forming γ-butyrolactones with three contiguous stereocenters. The addition occurs with high regio-, diastereo-, and enantiocontrol. This methodology constitutes an intermolecular DKR process to set three stereocenters during the key bond forming event.
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