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Asymmetric synthesis of oxindoles containing a quaternary stereogenic centre by catalytic O/C-carboxyl rearrangement
Authors:Muhammad Ismail  Gennadiy Ilyashenko  Christopher J Richards
Institution:a School of Chemical Sciences and Pharmacy, University of East Anglia, Norwich, NR4 7TJ, UK
b School of Biological and Chemical Sciences, Queen Mary, University of London, E1 4NS, UK
Abstract:A catalysed O/C-carboxyl rearrangement generates the all-carbon stereogenic centre in phenyl 1,3-dimethyl-5-methoxy-2-oxoindoline-3-carboxylate (up to 57% ee). Crystallisation and removal of racemic crystals enhance the ee to 95%. The X-ray crystal structure of the cobalt metallocene-pyrrolidinopyridine nucleophilic catalyst employed is reported.
Keywords:
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