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

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 journal › Article › peer-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 language	English
Pages (from-to)	3139-3142
Number of pages	4
Journal	Tetrahedron Letters
Volume	35
Publication status	Published - 1994

Fingerprint Dive into the research topics of 'Competing O-H insertion and  -elimination in rhodium carbenoid reactions; synthesis of 2-alkoxy-3-arylpropanoates'. Together they form a unique fingerprint.

Cite this

@article{a72fcc6902924aac8bca8d91be724c63,

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

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.",

author = "G.G. Cox and David Haigh and R.M. Hindley and D.J. Miller and C.J. Moody",

year = "1994",

language = "English",

volume = "35",

pages = "3139--3142",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

}

TY - JOUR

T1 - Competing O-H insertion and  -elimination in rhodium carbenoid reactions; synthesis of 2-alkoxy-3-arylpropanoates

AU - Cox, G.G.

AU - Haigh, David

AU - Hindley, R.M.

AU - Miller, D.J.

AU - Moody, C.J.

PY - 1994

Y1 - 1994

N2 - 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.

AB - 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.

M3 - Article

VL - 35

SP - 3139

EP - 3142

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

ER -