An efficient and practical preparation of optically active syn-1-vinyl-2-amino alcohol derivatives by the regio- and diastereoselective addition reaction of (γ-alkoxyallyl)titaniums with chiral imines. Formal synthesis of statine

(γ-Alkoxyallyl)titaniums 1, generated by the reaction of acrolein dialkyl acetals and a divalent titanium reagent (η2-propene)Ti(O-i-Pr)2, react readily with chiral imines 2, prepared from aldehydes and optically active 1-phenylethyl amine, in a regiospecific manner to give optically active syn-1-vinyl-2-amino alcohol derivatives 3 with diastereoselectivity of more than 80% in good yield. By using the adduct 3d thus obtained, statine was formally synthesized.