Direct Asymmetric Iodination of Aldehydes

Significance

The authors report an organocatalytic asymmetric iodination of aldehydes. Axially chiral bifunctional amino alcohol catalyst 1 has been found to be an efficient catalyst for this reaction. Diethyl ether was the best solvent for this reaction and N-iodosuccinimide (NIS) was used as the iodinating reagent. With 5 mol% of catalyst 1 and benzoic acid as an additive, high yields (76-98%) and excellent enantioselectivities (95:5 to >99:1 er) were obtained for different aldehydes.