Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 68, Issue 8, Pages 3112-3120Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo0268153
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A novel combined system of Yb(OTf)(3) with TMSCl or TMSOTf catalyzed an imino ene reaction. The reaction of N-tosylbenzaldimine (1) with cc-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.
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