Competing O - H insertion and β-elimination in rhodium carbenoid reactions; synthesis of 2-alkoxy-3-arylpropanoates

Article abstract of DOI:10.1016/S0040-4039(00)76851-1

Rhodium(II) carboxylate catalysed decomposition of diazo esters 3 and 4 in the presence of alcohols or water results in formation of 2-alkoxy- or 2-hydroxy-3-arylpropanoates respectively by O - H insertion in competition with cinnamates by elimination; the ratio of insertion to elimination is dramatically affected by the carboxylate ligand on rhodium. Use of methanol-d as the alcohol confirms that the alkene does not arise by elimination from the initial alkoxyester product.