Ni-catalyzed homoallylation of polyhydroxy N,O- Acetals with conjugated dienes promoted by triethylborane

Abstract

In the presence of Ni-catalyst and triethylborane, N,O- Acetals prepared from glycolaldehyde and glyceraldehyde with primary amines in situ underwent homoallylation with conjugated dienes to provide 2- Amino-5-hexenols in high regio- And stereoselectivity. Under similar reaction conditions, N,O- Acetals from carbohydrates with primary amines provided the corresponding polyhydroxy-bishomoallylamines in good to reasonable yields.