A Highly Efficient Ruthenium-Catalyzed Rearrangement of α,β-Epoxyketones to 1,2-Diketones

TpRuPPh3(CH3CN)2PF6 catalyzed the efficient rearrangement of α,β-epoxyketones to 1,2-diketones. Unlike a previously reported iron catalyst, the reaction in this case is applicable not only to 1,2-disubstituted epoxides but also to mono- and trisubstituted epoxides and tolerates oxygen functionalitie...

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Veröffentlicht in:Journal of organic chemistry 2004-04, Vol.69 (8), p.2793-2796
Hauptverfasser: Chang, Chia-Lung, Kumar, Manyam Praveen, Liu, Rai-Shung
Format: Artikel
Sprache:eng
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Zusammenfassung:TpRuPPh3(CH3CN)2PF6 catalyzed the efficient rearrangement of α,β-epoxyketones to 1,2-diketones. Unlike a previously reported iron catalyst, the reaction in this case is applicable not only to 1,2-disubstituted epoxides but also to mono- and trisubstituted epoxides and tolerates oxygen functionalities. The sterically crowded and highly basic tris(1-pyrazolyl)borate (Tp) ligand of the ruthenium catalyst might account for its high selectivity toward 1,2-diketone rather than 1,3-diketone.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0303867