Indium- or Zinc-Mediated One-Pot Synthesis of Homoallylamines, β-Amino Esters, and β-Amino Nitriles

<UFIGR ID="ol005912kn00001">Homoallylamines, β-amino esters, and β-amino nitriles were obtained in a one-pot synthesis directly from an aldehyde and a secondary amine such as dibenzylamine or diallylamine. Their condensation with titanium(IV) isopropoxide generates an intermediate aminoalkoxy titanium complex. Further reaction in THF with nucleophilic organometallic species, generated in situ from indium or zinc and a reactive halide (allyl bromide, alkyl bromo- or iodoacetate, iodoacetonitrile), furnished the corresponding amines.