Tetrahedron

Site selectivity in the rhodium (II)-catalyzed reaction of α-diazoimides. Ligand and substituent effects

M Prein, PJ Manley, A Padwa

Index: Prein, Michael; Manley, Peter J.; Padwa, Albert Tetrahedron, 1997 , vol. 53, # 23 p. 7777 - 7794

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Citation Number: 25

Abstract

The product distribution obtained from Rh (II)-catalyzed decomposition of α-diazoimides derived from glycine methyl ester has been found to be selectively controlled by the proper choice of catalyst. When the reaction was carried out using perfluorinated ligands, the diazoimide cyclized to produce an isomünchnone dipole whose formation could be monitored by NMR spectroscopy. Reaction of the dipole with a trapping agent such as N- ...