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

G.G. Cox, David Haigh, R.M. Hindley, D.J. Miller, C.J. Moody

Research output: Contribution to journalArticlepeer-review

Abstract

Rhodium(II) carboxylate catalyzed decompn. of diazo esters 3 (shown as I) and PhCH2C(CO2Et)N2 4 in the presence of alcs. or water results in formation of 2-alkoxy- or 2-hydroxy-3-arylpropanoates, resp., 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 alc. confirms that the alkene does not arise by elimination from the initial alkoxyester product.
Original languageEnglish
Pages (from-to)3139-3142
Number of pages4
JournalTetrahedron Letters
Volume35
Publication statusPublished - 1994

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