Diastereoselective Three-Component Coupling Synthesis of Homoallylic Amines

Significance

A highly regio- and diastereoselective one-pot method for the synthesis of branched homoallylic amines is reported in this article. The formation of two new stereocenters and two carbon-carbon bonds is achieved in one experimental operation. The reaction of an arylboronic acid with 1,2-nonadiene and Pd(OAc)₂/HP(t-Bu)₃BF₄ supposedly leads to an allylpalladium intermediate that attacks N-protected imines via Umpolung of its reactivity. Thus, branched homoallylic amines are obtained with >99% de seemingly in favor of the anti product. The conversion into substituted tetrahydropyridines via allylation of the nitrogen and subsequent metathesis demonstrates a possible applicability of this three-component coupling reaction in the syntheses of biologically active molecules.