ArticleAngewandte Chemie (International ed. in English)2014
Dynamic kinetic asymmetric transformations of β-stereogenic α-ketoesters by direct aldolization.
Article in Angewandte Chemie (International ed. in English), 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.
- Catalytic Enantioselective Methods for Synthesis of 1,2-Amino Tertiary Alcohols and Their Analogues.Chemical reviews · 2025Review
- Dynamic Kinetic Asymmetric Hydroacylation: Racemization by Soft Enolization.Journal of the American Chemical Society · 2025Article
- Synthesis of Difluorinated Halohydrins by the Chemoselective Addition of Difluoroenolates to α-Haloketones.Organic letters · 2021Article
- 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
- Cupreines and cupreidines: an established class of bifunctional cinchona organocatalysts.Beilstein journal of organic chemistry · 2016Review
- Enantioconvergent synthesis of functionalized γ-butyrolactones via (3 + 2)-annulation.Journal of the American Chemical Society · 2015Article
- Dynamic kinetic asymmetric cross-benzoin additions of β-stereogenic α-keto esters.Journal of the American Chemical Society · 2014Article
Corrections and comments
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Authors and funding
2 authors.
Funding
Abstract
Dynamic kinetic asymmetric transformations (DyKAT) of racemic β-bromo-α-keto esters by direct aldolization of nitromethane and acetone provide access to fully substituted α-glycolic acid derivatives bearing a β-stereocenter. The aldol adducts are obtained in excellent yield with high relative and absolute stereocontrol under mild reaction conditions. Mechanistic studies determined that the reactions proceed through a facile catalyst-mediated racemization of the β-bromo-α-keto esters under a DyKAT Type I manifold.
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