Titanocene-Promoted Intermolecular Couplings of Epoxides with Nitriles. An Easy Access to β-Hydroxyketones

Radical couplings of epoxides and nitriles mediated by Cp2TiCl provide a diastereoselective route to the synthesis of β-hydroxyketones. The conditions of this “aldol-like” reaction are mild enough to avoid the dehydration of the β-hydroxyketone. The scope of the coupling reaction with functionalized...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 74; no. 10; pp. 3913 - 3918
Main Authors Fernández-Mateos, A, Madrazo, S. Encinas, Teijón, P. Herrero, González, R. Rubio
Format Journal Article
LanguageEnglish
Published Washington, DC American Chemical Society 15.05.2009
Subjects
Aliphatic compounds
Chemistry
Exact sciences and technology
Free radicals chemistry
Organic chemistry
Preparations and properties
Reactivity and mechanisms
Nitrile
Ketol
Dehydration
Metallocene
Titanium III
Diastereoselectivity
Aldol condensation
Chemical coupling
Functionalization
Organic free radical
Titanium Organic compounds
Epoxide
Chemical synthesis
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Summary:Radical couplings of epoxides and nitriles mediated by Cp2TiCl provide a diastereoselective route to the synthesis of β-hydroxyketones. The conditions of this “aldol-like” reaction are mild enough to avoid the dehydration of the β-hydroxyketone. The scope of the coupling reaction with functionalized and tetrasubstituted epoxides has been studied. The radical character of the coupling reactions is demonstrated.
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo900479v