Titanocene(III) Chloride Mediated Radical Induced Allylation of Aldimines: Formal Synthesis of C-Linked 4′-Deoxy Aza-disaccharide

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 demonstra...

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Bibliographic Details
Published in:Journal of organic chemistry 2011-09, Vol.76 (17), p.7229-7234
Main Authors: Saha, Sumit, Roy, Subhas Chandra
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Alkaloids - chemistry
Allyl Compounds - chemistry
Amines - chemistry
Aza Compounds - chemistry
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Disaccharides - chemistry
Exact sciences and technology
Free Radicals
Free radicals chemistry
Models, Molecular
Molecular Structure
Organic chemistry
Organometallic Compounds - chemistry
Preparations and properties
Reactivity and mechanisms
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Summary: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 (Cp2TiCl2) and Zn dust in THF under argon.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo200908b