Asymmetric Arylation of Aldehydes with Polymer-Supported Amino Alcohols

Significance

Polymer-supported chiral β-amino alcohols 1 were prepared and used as chiral ligands in the enantioselective addition of organo­zinc reagents to aldehydes. The reaction of aliphatic and aromatic aldehydes with Et₂Zn proceeded in the presence of chlorotritylated polystyrene-supported amino alcohol 1a to give the corresponding alcohols in 50-95% yields and with 71-91% ee (Eq. 1). Arylation of the aldehydes with Ph₂Zn/Et₂Zn in the presence of the ligands 1b,c gave the alcohols with high enantioselectivity, while the arylation with ligand 1a resulted in products with low enantioselectivity (Eq. 2).