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Synthesis of a Ketorolac Model via Aromatic Carbenoid Insertion

Published in Helvetica Chimica Acta. 1998, vol. 81, no. 2, p. 317-323
Abstract The decomposition of diazo ester 2b with chiral RhII catalysts proceeded via intramolecular aromatic carbenoid insertion to the racemic pyrrole derivative 5b in 72% yield. In contrast, the benzoylated precursor 16 afforded no ketorolac 1b when exposed to RhII. Methyl 2‐diazo‐4‐phenylbutyrate (19), in turn, reacted, by 1,2‐hydrogen migration rather than by aromatic substitution, to 20.
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Other version: http://doi.wiley.com/10.1002/hlca.19980810212
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MULLER, Paul, POLLEUX, Philippe. Synthesis of a Ketorolac Model via Aromatic Carbenoid Insertion. In: Helvetica Chimica Acta, 1998, vol. 81, n° 2, p. 317-323. https://archive-ouverte.unige.ch/unige:121104

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