Novel chiral thiazoline‐containing N―O ligands in the asymmetric addition of diethylzinc to aldehydes: substituent effect on the enantioselectivity

Several novel chiral thiazoline primary and tertiary alcohols were easily synthesized from commercially available l ‐cysteine in three steps and with high yield. These ligands were subsequently applied to the asymmetric addition of diethylzinc (Et₂Zn) to various aldehydes. Products with S configuration were obtained when thiazoline‐containing tertiary alcohol ligands were used as catalysts. The primary alcohol induced corresponding products with R configuration in 68% enantiomeric excess, which was a higher value relative to other N―O ligands possessing a primary alcohol unit in the literature. Furthermore, a plausible transition state model was proposed to explain the observed enantioselectivities. Copyright © 2012 John Wiley & Sons, Ltd.