Asymmetric Proline‐Catalyzed Addition of Aldehydes to 3H‐Indol‐3‐ones: Enantioselective Synthesis of 2,3‐Dihydro‐1H‐indol‐3‐ones with Quaternary Stereogenic Centers |
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Authors: | Magnus Rueping Ramesh Rasappan Sadiya Raja |
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Affiliation: | Institute of Organic Chemistry, RWTH‐Aachen University, Landoltweg 1, DE‐52074 Aachen, (fax +49(241)8092665) |
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Abstract: | The proline‐catalyzed addition of various aliphatic aldehydes to sterically hindered 2‐aryl‐substituted 3H‐indol‐3‐ones affords 2,2‐disubstituted 2,3‐dihydro‐1H‐indol‐3‐one derivatives with excellent enantioselectivities. In addition, the synthesis of a chiral derivative, (S)‐2‐(2‐bromophenyl)‐2,3‐dihydro‐2‐(2‐hydroxyethyl)‐1H‐indol‐3‐one, which can be used as an intermediate for the preparation of the natural product hinckdentine A was accomplished with a high level of enantioselectivity. |
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Keywords: | Catalysis Mannich reaction Proline Indol‐2‐acetaldehyde Hinckdentine A |
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