ArticleJournal of the American Chemical Society2014
Dynamic kinetic asymmetric cross-benzoin additions of β-stereogenic α-keto esters.
Article in Journal of the American Chemical Society, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 77 citations in OpenAlex.
- Catalytic Enantioselective Methods for Synthesis of 1,2-Amino Tertiary Alcohols and Their Analogues.Chemical reviews · 2025Review
- Dynamic kinetic resolution of γ,γ-disubstituted indole 2-carboxaldehydesChemical science · 2022Article
- Article
- 2-Azadienes as Reagents for Preparing Chiral Amines: Synthesis of 1,2-Amino Tertiary Alcohols by Cu-Catalyzed Enantioselective Reductive Couplings with Ketones.Journal of the American Chemical Society · 2018Article
- 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
- Recent advances in N-heterocyclic carbene (NHC)-catalysed benzoin reactions.Beilstein journal of organic chemistry · 2016Review
- Enantioconvergent synthesis of functionalized γ-butyrolactones via (3 + 2)-annulation.Journal of the American Chemical Society · 2015Article
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
The dynamic kinetic resolution of β-halo α-keto esters via an asymmetric cross-benzoin reaction is described. A chiral N-heterocyclic carbene catalyzes the umpolung addition of aldehydes to racemic α-keto esters. The resulting fully substituted β-halo glycolic ester products are obtained with high levels of enantio- and diastereocontrol. The high chemoselectivity observed is a result of greater electrophilicity of the α-keto ester toward the Breslow intermediate. The reaction products are shown to undergo highly diastereoselective substrate-controlled reduction to give highly functionalized stereotriads.
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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.