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Imino Ene Reaction Catalyzed by Ytterbium(III) Triflate and TMSCl or TMSOTf

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journal contribution
posted on 19.03.2003, 00:00 by Masamichi Yamanaka, Atsushi Nishida, Masako Nakagawa
A novel combined system of Yb(OTf)3 with TMSCl or TMSOTf catalyzed an imino ene reaction. The reaction of N-tosylbenzaldimine (1) with α-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 α-methylstyrene in the presence of Yb(OTf)3 and TMSOTf, to give the corresponding homoallylic amine.