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

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 successfull...

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Bibliographic Details
Published in:Journal of organic chemistry 2003-04, Vol.68 (8), p.3112-3120
Main Authors: Yamanaka, Masamichi, Nishida, Atsushi, Nakagawa, Masako
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0268153