A Novel "Ti(0)" Induced Allylation of Imines in a TiCl₄(cat.)/Al Bimetal System. Chirality Transfer of l-Valine to Homoallylamine

Tanaka, H.; Inoue, K.; Pokorski, U.; Taniguchi, M.; Torii, S. Tetrahedron Lett. 1990, 31, 3023.

"Barbier Type" allylation of imines with allyl bromide has been performed successfully by the action of aluminium (1 equiv.) and titanium(IV) chloride (0.05 equiv.) in THF. The chirality transfer of a-amino acid esters to homoallyl amines is demonstrated by allylation of N-benzalvaline methyl ester followed by alkaline hydrolysis and electrolytic decarboxylation.