Helvetica chimica acta

Synthesis of a ketorolac model via aromatic carbenoid insertion

P Müller, P Polleux

Index: Mueller, Paul; Polleux, Philippe Helvetica Chimica Acta, 1998 , vol. 81, # 2 p. 317 - 323

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Citation Number: 14

Abstract

Abstract The decomposition of diazo ester 2b with chiral Rh II 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 Rh II. Methyl 2-diazo-4-phenylbutyrate (19), in turn, reacted, by 1, 2-hydrogen migration rather than by aromatic substitution, to 20.