A complete study of the asymmetric addition of phenylacetylene to ketones catalyzed by Schiff-base amino alcohol-Zn complex is reported in this article. The Schiff-base amino alcohols were easily prepared from amino acids in three steps. When the amount of ligand was 1%（molar fraction）, an e.e. value up to 94% was obtained. A series of practical chiral ligands were applied in the enantioselective addition of phenylacetylene to ketones without adding another stronger Lewis acid except zinc.
A readily availableβ-sulfonamide alcohol-titanium complex was found to be effective on promoting the asymmetric addition reaction of an alkynylzinc reagent to unactivated simple ketones under very mild conditions.And the corresponding chiral tertiary propargylic alcohols were obtained with enantiomeric excesses of up to 86%,which provided a simple,practical and inexpensive method to generate chiral tertiary propargylic alcohols.
