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Asymmetric Proline‐Catalyzed Addition of Aldehydes to 3 H ‐Indol‐3‐ones: Enantioselective Synthesis of 2,3‐Dihydro‐1 H ‐indol‐3‐ones with Quaternary Stereogenic Centers
Author(s) -
Rueping Magnus,
Rasappan Ramesh,
Raja Sadiya
Publication year - 2012
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201200498
Subject(s) - chemistry , stereocenter , enantioselective synthesis , proline , steric effects , catalysis , stereochemistry , natural product , derivative (finance) , medicinal chemistry , organic chemistry , amino acid , biochemistry , financial economics , economics
The proline‐catalyzed addition of various aliphatic aldehydes to sterically hindered 2‐aryl‐substituted 3 H ‐indol‐3‐ones affords 2,2‐disubstituted 2,3‐dihydro‐1 H ‐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)‐1 H ‐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.