Yamanaka Masamichi, Nishida Atsushi, Nakagawa Masako
Graduate School of Pharmaceutical Sciences, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan.
J Org Chem. 2003 Apr 18;68(8):3112-20. doi: 10.1021/jo0268153.
A novel combined system of Yb(OTf)(3) with TMSCl or TMSOTf catalyzed an imino ene reaction. The reaction of N-tosylbenzaldimine (1) with alpha-methylstyrene (2) proceeded smoothly to give homoallylic amine 3 in the presence of a catalytic amount of Yb(OTf)(3) and TMSCl. This catalytic system was successfully applied to the imino ene reactions of various aldimines with alkenes. This new imino ene reaction provides a unique method for the three-component coupling reaction of an aldehyde, tosylamide, and alpha-methylstyrene in the presence of Yb(OTf)(3) and TMSOTf, to give the corresponding homoallylic amine.
一种由Yb(OTf)₃与TMSCl或TMSOTf组成的新型复合体系催化亚氨基烯反应。在催化量的Yb(OTf)₃和TMSCl存在下，N-对甲苯磺酰基苯甲醛亚胺(1)与α-甲基苯乙烯(2)的反应顺利进行，生成高烯丙基胺3。该催化体系成功应用于各种醛亚胺与烯烃的亚氨基烯反应。这种新的亚氨基烯反应为在Yb(OTf)₃和TMSOTf存在下醛、对甲苯磺酰胺和α-甲基苯乙烯的三组分偶联反应提供了一种独特的方法，以生成相应的高烯丙基胺。
