Highly enantioselective phenylacetylene additions to both aliphatic and aromatic aldehydes

[GRAPHICS] The readily available and inexpensive BINOL in combination with Ti((OPr)-Pr-i)(4) is found to catalyze the reaction of an alkynylzinc reagent with various types of aldehydes including aliphatic aldehydes, aromatic aldehydes, and other alpha,beta-unsaturated aldehydes to generate chiral propargyl alcohols with 91-99% ee at room temperature. No previous chiral catalysts have exhibited such a broad scope of enantioselectivity with respect to the type of aldehydes for this reaction.