Asymmetric synthesis of oxindoles containing a quaternary stereogenic centre by catalytic O/C-carboxyl rearrangement |
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Authors: | Muhammad Ismail Gennadiy Ilyashenko Christopher J Richards |
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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 |
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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. |
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