Copper-Catalyzed Tandem [2,3]-Rearrangement and 6π-3-Azatriene Electrocyclization in ( E ) -O -Propargylic α,β-Unsaturated Oximes
2010; American Chemical Society; Volume: 132; Issue: 23 Linguagem: Inglês
10.1021/ja102436z
ISSN1943-2984
AutoresItaru Nakamura, Dong Zhang, Masahiro Terada,
Tópico(s)Click Chemistry and Applications
ResumoCu-catalyzed cyclizations of (E)-O-propargylic oximes of alpha,beta-unsaturated aldehydes were successfully carried out to afford the corresponding pyridine oxides in good to high yields. As an example, (E)-acrylaldehyde O-1,3-diphenylprop-2-ynyl oxime (1b) was reacted for 5 h in the presence of CuBr(PPh(3))(3) (10 mol %) and PPh(3) (10 mol %) in DMSO at 120 degrees C to afford 3-benzyl-2-phenylpyridine-N-oxide (2b) in 84% yield. In this case, the reaction proceeded via Cu-catalyzed propargyl oxime-allenyl nitrone rearrangement followed by 6pi-3-azatriene electrocyclization.
Referência(s)