Indium- or zinc-mediated one-pot synthesis of homoallylamines, beta-amino esters, and beta-amino nitriles

Homoallylamines, beta-amino esters, and beta-amino nitriles were obtained i n a one pot synthesis directly from an aldehyde and a secondary amine such as dibenzylamine or diallylamine. Their condensation with titanium(IV) isop ropoxide generates an intermediate aminoalkoxy titanium complex. Further re action in THF with nucleophilic organometallic species, generated in situ f rom indium or zinc and a reactive halide (allyl bromide, alkyl bromo- or io doacetate, iodoacetonitrile), furnished the corresponding amines.