Camphor-based Schiff base ligand SBAIB: an enantioselective catalyst for addition of phenylacetylene to aldehydes

A series of Schiff base ligands were synthesized from (1R)-camphor. Under the optimal conditions, (+)-SBAIB-a, 10 was found to be an excellent catalyst for the enantioselective addition of phenylacetylene to various aldehydes without utilizing either achiral additives or Ti((OPr)-Pr-i)(4). This approach yielded (R)-propargylic alcohols in extremely high yields (up to 99%) and excellent enantioselectivities (up to 92%). The corresponding (S)-propargylic alcohols were synthesized in good to high enantioselectivities (up to 91%) and excellent yields (up to 99%) using (-)-SBAIB-a, 41.