Miyabe Hideto, Yamaoka Yousuke, Naito Takeaki, Takemoto Yoshiji
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
J Org Chem. 2003 Aug 22;68(17):6745-51. doi: 10.1021/jo034451o.
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.
研究了在催化量的钯（0）配合物和碘化铟（I）存在下，缺电子亚胺与烯丙醇衍生物的烯丙基化反应。在具有樟脑磺内酰胺的乙醛肟醚反应中观察到烯丙基化的可逆性。作为水对区域选择性的重要影响，在水存在下，单取代烯丙基试剂动力学上形成γ-加合物。在无水四氢呋喃中观察到热力学稳定的α-加合物的选择性形成。相比之下，即使在无水反应条件下，N-磺酰亚胺的烯丙基化也能以高区域选择性得到γ-加合物。
