857087-98-0Relevant academic research and scientific papers
An imino-Diels-Alder route to meso-2,6-disubstituted-4-piperidones
García, Ana-Belén,Valdés, Carlos,Cabal, María-Paz
, p. 4357 - 4360 (2004)
A convenient stereoselective preparation of meso-2,6-disubstituted-4- piperidones has been developed by imino-Diels-Alder reaction of 2-amino-1,3-butadienes with imines in the presence of catalytic amount of Cu(TfO)2.
New reaction of enamines with aryldiazoacetates catalyzed by transition metal complexes
Zhao, Wei-Jie,Yan, Ming,Huang, Dan,Ji, Shun-Jun
, p. 5585 - 5593 (2007/10/03)
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.
Palladium catalyzed animation of vinyl chlorides: A new entry to imines, enamines and 2-amino-1,3-butadienes
Barluenga, Jose,Fernandez, M. Alejandro,Aznar, Fernando,Valdes, Carlos
, p. 1400 - 1401 (2007/10/03)
Vinyl chlorides are employed for the first time in palladium catalyzed cross-coupling reactions with amines to furnish imines and enamines. The new methodology has been applied to the synthesis of 2-amino-1,3-butadienes, that could not be achieved from th
