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- W2785838066 abstract "Chiral α-hydroxycarboxylic acids and their derivatives bearing a tetrasubstituted α-carbon atom are well-recognized chiral synthons and components of various pharmaceuticals and biologically active natural products. Despite their high demand, preparative methods of these compounds are quite limited due to the difficulty in achieving stereoselective construction of the tetrasubstituted carbon stereogenic center at the α-position. To address this issue, we developed asymmetric nucleophilic addition reactions of 5H-oxazol-4-ones to carbon electrophiles using chiral bicyclic guanidine catalysts containing a hydroxyl group at the appropriate position as a preparative method of α-tetrasubstituted hydroxycarboxylic acid derivatives. In this article, we introduce the nucleophilic addition reactions with several types of electrophiles, such as aldehydes, alkynyl carbonyl compounds, allenyl carbonyl compounds, vinyl ketones, dienones, and 2-chloroacrylnitrile. Derivatizations of the products of these reactions into corresponding α-hydroxycarboxylic acid derivatives and their application to a natural product synthesis are also described." @default.
- W2785838066 created "2018-02-23" @default.
- W2785838066 creator A5016881633 @default.
- W2785838066 creator A5023728228 @default.
- W2785838066 date "2018-01-01" @default.
- W2785838066 modified "2023-10-18" @default.
- W2785838066 title "Chiral Guanidines-catalyzed Nucleophilic Addition Reactions Using 5<i>H</i>-Oxazol-4-ones: Development of Catalytic Asymmetric Syntheses of Chiral α-Tetrasubstituted Hydroxycarboxylic Acid Derivatives" @default.
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- W2785838066 doi "https://doi.org/10.5059/yukigoseikyokaishi.76.137" @default.
- W2785838066 hasPublicationYear "2018" @default.
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