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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
Authors:Magnus Rueping  Ramesh Rasappan  Sadiya Raja
Affiliation:Institute of Organic Chemistry, RWTH‐Aachen University, Landoltweg 1, DE‐52074 Aachen, (fax +49(241)8092665)
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.
Keywords:Catalysis  Mannich reaction  Proline  Indol‐2‐acetaldehyde  Hinckdentine A
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