Chemistry is the experimental and theoretical study of materials on their properties at both the macroscopic and microscopic levels.In a patent， Quality Control of: tert-Butyl 3-(2-methoxy-2-oxoethyl)-1H-indole-1-carboxylate, Which mentioned a new discovery about 370562-34-8
The reaction of aryldiazoacetates with enamines catalyzed by copper and rhodium complexes provided gamma-keto esters in good yields. A full investigation of the effects of solvents, catalysts, enamines and aryldiazoacetates on the reaction was carried out. Careful analysis of the crude reaction mixture revealed a substituted enamine as the primary product, which was hydrolyzed over silica gel to give a gamma-keto ester as the final product. A reaction mechanism involving nucleophilic addition of an enamine to a metal carbene and subsequent hydrogen transfer was proposed. Chiral dirhodium and copper catalysts were examined and found to provide gamma-keto esters with no enantioselectivity. The result could be rationalized based on the proposed reaction mechanism. Attempts to trap the enamine intermediate with several electrophilic reagents were not successful.
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Reference：
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles