A highly enantioselective [4+2] cycloaddition involving aldehydes and β,γ-unsaturated-α-keto esters |
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Authors: | Nanda Kumar Katakam Yejin Kim Allan D Headley |
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Institution: | Department of Chemistry, Texas A&M University-Commerce, Commerce, TX 75429-3011, USA |
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Abstract: | A stereoselective inverse electron demand oxo-Diels-Alder reaction involving electron poor dienes (γ-aryl-β,γ-unsaturated-α-keto ester) and electron rich dienophiles has been studied. These cycloaddition reactions are extremely useful for the construction of O-, N-, S-centered heterocyclic compounds, which are routinely used in both synthetic organic and medicinal chemistry. The 4+2] hetero cycloaddition reactions involving various aldehydes and β,γ-unsaturated-α-keto esters were carried out in which three different types of substituted proline catalysts were examined. For these reactions, high selectivities (enantiomeric excess 93–98%) were obtained using catalyst 3. Due to the bulkiness of catalyst 3, compared to the other catalysts tested, it is more efficient at catalyzing these type reactions. |
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Keywords: | Corresponding author |
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