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Palladium-Catalyzed, One-Pot, Three-Component Synthesis of Homoallylic Amines from Aldehydes, Anisidine, and Allyl Trifluoroacetate

Robin E. Grote and Elizabeth R. Jarvo*

*Natural Sciences I 4114, Department of Chemistry, University of California, Irvine, Irvine California 92697, Email: erjarvouci.edu

R. E. Grote, E. R. Jarvo, Org. Lett., 2009, 11, 485-488.

DOI: 10.1021/ol8026297 (free Supporting Information)


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Abstract

A palladium complex catalyzes two transformations in one pot: formation of allylsilane from allyl trifluoroacetate using hexamethyldisilane and subsequent imine allylation. A three-component reaction was developed where preformed imines were replaced with aldehydes and anisidine. Under these reaction conditions various aldehydes react smoothly to afford homoallylic amines.

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Key Words

Homoallylic Amines (C-C Coupling, Amination), Multicomponent Reactions


ID: J54-Y2009-0320