title: Titanocene(III) chloride mediated radical induced allylation of aldimines: formal synthesis of C-linked 4'-deoxy aza-disaccharide.
abstract: Titanocene(III) chloride (Cp(2)TiCl) mediated radical induced allylation of aldimines for the preparation of homoallyl amines is described. The radical was generated from the allyl bromide using Cp(2)TiCl 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 Cp(2)TiCl was prepared in situ from commercially available titanocene dichloride (Cp(2)TiCl(2)) and Zn dust in THF under argon.
authors.affiliation: Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700032, India.
authors.forename: Sumit
authors.initials: S
authors.lastname: Saha
authors.forename: Subhas Chandra
authors.initials: SC
authors.lastname: Roy
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000470:Alkaloids / Q000737:chemistry; D000498:Allyl Compounds / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D001372:Aza Compounds / Q000737:chemistry*; D004187:Disaccharides / Q000737:chemistry*; D005609:Free Radicals; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D000470:Alkaloids; D000498:Allyl Compounds; D000588:Amines; D001372:Aza Compounds; D004187:Disaccharides; D005609:Free Radicals; D009942:Organometallic Compounds; C020528:titanocene dichloride