Stereoselective Reductive Coupling of Chiral Sulfinyl Imines with Aldehydes

Significance

A reductive cross-coupling reaction between aliphatic aldehydes and chiral N-tert-butanesulfinimines in the presence of SmI₂ leads to the formation of β-amino alcohols with excellent enantiomeric and diastereomeric excesses and good yields. The products can be used as chiral ligands or auxiliaries in asymmetric synthesis. The method allows also the preparation of important natural compounds like statine, a structural moiety of novel protease blockers, very perspective for pharmacology.