55949-66-1Relevant articles and documents
New reaction of enamines with aryldiazoacetates catalyzed by transition metal complexes
Zhao, Wei-Jie,Yan, Ming,Huang, Dan,Ji, Shun-Jun
, p. 5585 - 5593 (2005)
The reaction of aryldiazoacetates with enamines catalyzed by copper and rhodium complexes provided γ-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 γ-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 γ-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.
Synthesis of enamines using easily prepared silica gel supported sulfuric acid catalyst
Bigdeli, Mohammad Ali,Nikje, Mir Mohammad Alavi,Gorji, Banafshe,Moghimi, Aboulghasem
, p. 800 - 801 (2007/10/03)
A variety of enamines are easily and efficiently synthesised in short reaction times and moderate to high yields from corresponding acyclic and cyclic ketones using sulfuric acid-silica catalyst.
