Ligand effects in the rhodium (II)-catalyzed reactions of. alpha.-diazoamides. oxindole formation is promoted by the use of rhodium (II) perfluorocarboxamide catalysts

…, CJ Moody, TJ Mowlem, JPJ Marino…

Index: Brown, David S.; Elliott, Mark C.; Moody, Christopher J.; Mowlem, Timothy J.; Marino, Joseph P.; Padwa, Albert Journal of Organic Chemistry, 1994 , vol. 59, # 9 p. 2447 - 2455

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Citation Number: 99

Abstract

An improved procedure for the preparation of ethyl 2-diazomalonyl chloride was developed which involves the reaction of ethyl diazoacetate with triphosgene. Using this diazo acid chloride, it was possible to prepare a variety of diazoamides from substituted amines. The rhodium (I1)-catalyzed decomposition of these diazoamides was studied in order toprobe the chemoselectivity of the carbenoid intermediates in intramolecular insertion reactions. ...