861395-39-3Relevant academic research and scientific papers
Selective synthesis of allylated oxime ethers and nitrones based on palladium-catalyzed allylic substitution of oximes
Miyabe, Hideto,Yoshida, Kazumasa,Reddy, Valluru Krishna,Matsumura, Akira,Takemoto, Yoshiji
, p. 5630 - 5635 (2005)
The viability of oximes as nucleophiles in transition-metal-catalyzed allylic substitution was examined. The oxygen atom of oxime acted as a reactive nucleophile in the reaction of a π-allyl palladium complex. In the presence of Pd(PPh3)4, the allylic substitution of oximes with allylic carbonate afforded the linear O-allylated oxime ethers selectively without a base. In contrast, the palladium-catalyzed reaction with allylic acetate proceeded smoothly in the presence of K2CO3 or Et2Zn as a base. Selective formation of nitrones was achieved by using palladium(II) catalyst. In the presence of Pd(cod)Cl2, the allylic substitution of oximes with allylic acetate afforded the N-allylated nitrones under solvent-free conditions, as a result of the reaction with the nitrogen atom of oximes.
Synthesis of chiral oxime ethers based on regio- and enantioselective allylic substitution catalyzed by iridium-pybox complex
Miyabe, Hideto,Matsumura, Akira,Yoshida, Kazumasa,Takemoto, Yoshiji
experimental part, p. 4464 - 4470 (2009/10/02)
The oxygen atom of oximes acts as a reactive nucleophile in the iridium-catalyzed allylic substitution of unsymmetrical substrates to give the branched oxime ethers. Among several chiral ligands evaluated, the iridium complex of pybox ligand having phenyl
Novel synthesis of O-allylated oxime ethers based on allylic substitution with oximes
Miyabe, Hideto,Matsumura, Akira,Yoshida, Kazumasa,Yamauchi, Masashige,Takemoto, Yoshiji
, p. 2123 - 2126 (2007/10/03)
The palladium or iridium-catalyzed O-allylic substitution of oximes provides a new method for direct preparation of the O-allylated oxime ethers from oximes.
