Asymmetric synthesis of homoallylic amines via 1,2-addition of Grignard reagent to aliphatic N-phosphonyl hemiaminal

Abstract

A general method for asymmetric synthesis of alkylated homoallylic amines was developed via a one-pot three-component reaction of easily available N-phosphonyl amides, aliphatic aldehydes, and allylic Grignard reagents. As anticipated the reaction proceeds through six-membered chelation controlled mechanism, allowing 1,2-nucleophilic addition to directly give chiral homoallylic amines with high yields and excellent diastereoselectivity.