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Catalytic Enantioselective 1,3‐Alkyl Shift in Alkyl Aryl Ethers: Efficient Synthesis of Optically Active 3,3′‐Diaryloxindoles
Author(s) -
Gade Amol B.,
Bagle Pradip N.,
Shinde Popat S.,
Bhardwaj Vipin,
Banerjee Subhrashis,
Chande Ajit,
Patil Nitin T.
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201801650
Subject(s) - alkyl , enantioselective synthesis , hela , aryl , catalysis , enantiomer , chemistry , enantiomeric excess , optically active , organic chemistry , in vitro , biochemistry
Reported is the first organocatalytic asymmetric 1,3‐alkyl shift in alkyl aryl ethers for the synthesis of chiral 3,3′‐diaryloxindoles using a chiral Brønsted acid catalyst. Preliminary results showed that each enantiomer of the 3,3′‐diaryloxindole, and a racemic mixture, showed different antiproliferative activities against HeLa cell lines by using an MTT assay.