Abstract
The product ratio of intermolecular insertion and cyclopropanation in transition metal-catalyzed diazo decompositions depends strongly upon the metal, its ligands and upon the substituents of the diazo compound. Ethyl diazoacetate ( 2a) reacts with cyclohexene ( 1) almost exclusively by cyclopropanation. However, diazomalonate ( 2d) and methyl 2-diazophenylacetate ( 2e) in the presence of Rh II catalysts exhibit a marked tendency towards allylic CH insertion. With 1,4-cyclohexadiene ( 6), methyl 2-diazophenylacetate ( 2e) in the presence of chiral Rh II catalysts affords the allylic insertion product 7 in almost quantitative yield and with up to 74% ee.
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