ArticleJournal of the American Chemical Society2021
Stereodivergent Nucleophilic Additions to Racemic β-Oxo Acid Derivatives: Fast Addition Outcompetes Stereoconvergence in the Archetypal Configurationally Unstable Electrophile.
Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Inductive Diastereoselective Rationale for a Catalytic Strategy to Build Densely Chiral Five-Membered Carbocycles.JACS Au · 2026Article
- Rh-Catalyzed Chemodivergent Parallel Kinetic Resolution and Desymmetrization of Enynes and Dienynes with Acrylamides.Angewandte Chemie (International ed. in English) · 2026Article
- Divergent Synthesis of Chiroptical Molecular Switches Based on 1,2-Diaxial Atropisomers.JACS Au · 2024Article
- Remote 1,4-Carbon-to-Carbon Boryl Migration: From a Mechanistic Challenge to a Valuable Synthetic Application of Bicycles.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- EnantioconvergentOrganic letters · 2023Article
- Mechanism of a Dually Catalyzed Enantioselective Oxa-Pictet-Spengler Reaction and the Development of a Stereodivergent Variant.ACS catalysis · 2023Article
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Authors and funding
4 authors.
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Abstract
Additions of carbon nucleophiles to racemic α-stereogenic β-oxo acid derivatives that deliver enantiomerically enriched tertiary alcohols are valuable, but uncommon. This article describes stereodivergent Cu-catalyzed borylative cyclizations of racemic β-oxo acid derivatives bearing tethered pro-nucleophilic olefins to deliver highly functionalized cyclopentanols containing four contiguous stereogenic centers. The reported protocol is applicable to a range of β-oxo acid derivatives, and the diastereomeric products are readily isolable by typical chromatographic techniques. α-Stereogenic-β-keto esters are typically thought to have extreme or spontaneous configurational fragility, but mechanistic studies for this system reveal an unusual scenario wherein productive catalysis occurs on the same time scale as background substrate racemization and completely outcompetes on-cycle epimerization, even under the basic conditions of the reaction.
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