Titanocene(III) chloride mediated radical induced allylation of aldimines: Formal synthesis of C-linked 4′-deoxy aza-disaccharide

Article abstract of DOI:10.1021/jo200908b

Titanocene(III) chloride (Cp₂TiCl) mediated radical induced allylation of aldimines for the preparation of homoallyl amines is described. The radical was generated from the allyl bromide using Cp₂TiCl as the radical source. Formal synthesis of C(4)-C(5′)-linked 4′-deoxy aza-disaccharide is demonstrated and a study toward the bicyclic skeleton of alkaloids was also accomplished. The radical initiator Cp₂TiCl was prepared in situ from commercially available titanocene dichloride (Cp ₂TiCl₂) and Zn dust in THF under argon.