Regioselectivity in palladium-indium iodide-mediated allylation reaction of glyoxylic oxime ether and N-sulfonylimine.
Allylation reaction of electron-deficient imines with allylic alcohol derivatives in the presence of a catalytic amount of palladium(0) complex and indium(I) iodide was studied. The reversibility of allylation was observed in the reaction of glyoxylic oxime ether having camphorsultam. As the important effect of water on regioselectivity, the gamma-adducts were kinetically formed from monosubstituted allylic reagents in the presence of water. The selective formation of thermodynamically stable alpha-adducts was observed in anhydrous THF. In contrast, the allylation of N-sulfonylimine gave the gamma-adducts with high regioselectivities even under anhydrous reaction conditions.
Miyabe
Hideto
H
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
Yamaoka
Yousuke
Y
Naito
Takeaki
T
Takemoto
Yoshiji
Y
D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D004987:Ethers / Q000737:chemistry*; D006038:Glyoxylates / Q000138:chemical synthesis* / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007202:Indicators and Reagents; D007204:Indium; D007454:Iodides; D008968:Molecular Conformation; D010091:Oximes / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium; D012997:Solvents; D013450:Sulfones / Q000737:chemistry*
D000498:Allyl Compounds; D004987:Ethers; D006038:Glyoxylates; D007097:Imines; D007202:Indicators and Reagents; D007454:Iodides; C482356:N-sulfonylimine; D010091:Oximes; D012997:Solvents; D013450:Sulfones; C482355:glyoxylic oxime ether; D007204:Indium; D010165:Palladium