Tetrahedron Letters p. 3139 - 3142 (1994)
Update date:2022-07-31
Topics:
Cox, Geoffrey G.
Haigh, David
Hindley, Richard M.
Miller, David J.
Moody, Christopher J.
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.
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