2-Amino-1-phenyl-1,3-propanediol Derivatives. New Ligands for Asymmetric 1,4-Addition of Organozinc Reagents to Enones

Abstract
In the presence of (1S,2S)-3-benzyloxy-2-morpholino-1-phenylpropanol derived readily from (1S,2S)-2-amino-1-phenyl-1,3-propanediol and nickel acetylacetonate, diethylzinc added to α,β-unsaturated ketones to give alkylated product in high optical purity (up to 95%ee). The effects of solvents and additives and the use of such ligands as a chiral catalyst were also investigated.