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The Journal of organic chemistry

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


PMID 21793531

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.

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234826
Bis(cyclopentadienyl)titanium(IV) dichloride, 97%
C10H10Cl2Ti