A novel chiral diallylic diamine has been synthesized through double addition of allyl zinc bromide to chiral imines in this contribution. Firstly, (S)-N-Boc-2-amino-3-phenylpropanal was prepared through N-Boc protection and Dess-Martin oxidation. Then, it was condensed with (S)-valine methyl ester to form a chiral imine, which was reacted with allyl zinc bromide in the presence of CeC1₃•7H₂O to afford the corresponding chiral homoallylic amine with high optical activity. After removing Boc group, the newly formed chiral homoallylic amine was condensed with 2-thiophenecarboxaldehyde to provide a novel chiral imine with high optical purity. The following asymmetric addition of allyl zinc bromide to the novel chiral imine provided the target compound. The structure and the purity of desired compound and the key intermediates were demonstrated by ¹H NMR, ¹³C NMR and MS spectra.

Key words: imine, chiral diamine, allyl bromide, asymmetric addition, chiral α-amino aldehyde