ArticleAngewandte Chemie (International ed. in English)2015
Enantioselective desymmetrization of prochiral cyclohexanones by organocatalytic intramolecular Michael additions to α,β-unsaturated esters.
Article in Angewandte Chemie (International ed. in English), 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Switchable organocatalytic enantioselective sulfenocyclization of cyclohexadienes enabling chemodivergent access to chiral bicyclo[m.n.1] ring systems.Nature communications · 2025Article
- Quantum chemical calculations for reaction prediction in the development of synthetic methodologies.Chemical science · 2023Review
- Enantioselective Total Synthesis of (-)-Himalensine A via a Palladium and 4-Hydroxyproline Co-catalyzed Desymmetrization of Vinyl-bromide-tethered Cyclohexanones.Journal of the American Chemical Society · 2023Article
- OSCAR: an extensive repository of chemically and functionally diverse organocatalysts.Chemical science · 2022Article
- A New Organocatalytic Desymmetrization Reaction Enables the Enantioselective Total Synthesis of Madangamine E.Journal of the American Chemical Society · 2022Article
- A modular and divergent approach to spirocyclic pyrrolidines.Chemical science · 2020Article
- Dual catalytic enantioselective desymmetrization of allene-tethered cyclohexanones.Chemical science · 2020Article
- Site-Selective Reaction of Enaminones and Enamine Esters for the Synthesis of Novel Diverse Morphan Derivatives.ACS omega · 2018Article
- (Thio)urea-mediated synthesis of functionalized six-membered rings with multiple chiral centers.Beilstein journal of organic chemistry · 2016Review
- Enantioselective synthesis of bicyclo[3.n.1]alkanes by chiral phosphoric acid-catalyzed desymmetrizing Michael cyclizations.Chemical science · 2015Article
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6 authors.
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Abstract
A new catalytic asymmetric desymmetrization reaction for the synthesis of enantioenriched derivatives of 2-azabicyclo[3.3.1]nonane, a key motif common to many alkaloids, has been developed. Employing a cyclohexanediamine-derived primary amine organocatalyst, a range of prochiral cyclohexanone derivatives possessing an α,β-unsaturated ester moiety linked to the 4-position afforded the bicyclic products, which possess three stereogenic centers, as single diastereoisomers in high enantioselectivity (83-99% ee) and in good yields (60-90%). Calculations revealed that stepwise C-C bond formation and proton transfer via a chair-shaped transition state dictate the exclusive endo selectivity and enabled the development of a highly enantioselective primary amine catalyst.
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