Addition of allylmetal reagents to the imine derived from 2-pyridine carboxaldehyde and methyl (S)-valinate. Synthesis of (S)- and (R)-1-(2-pyridyl)-3-butenamine

Article abstract of DOI:10.1016/0957-4166(96)00251-0

Allylmetal reagents add to the imine derived from 2-pyridine carboxaldehyde and methyl (S)-valinate or to preformed imine-metal salt complexes to give mainly the S,S- or the R,S-secondary homoallylic amine, depending on the nature of the allylmetal reagents. Both the (S)- and (R)-1-(2-pyridyl)-3-butenamine were prepared with high enantiomeric purity by removal of the auxiliary group.