A highly efficient ruthenium-catalyzed rearrangement of alpha,beta-epoxyketones to 1,2-diketones

Chia-Lung Chang; Manyam Praveen Kumar; Rai-Shung Liu

doi:10.1021/jo0303867

A highly efficient ruthenium-catalyzed rearrangement of alpha,beta-epoxyketones to 1,2-diketones

J Org Chem. 2004 Apr 16;69(8):2793-6. doi: 10.1021/jo0303867.

Authors

Chia-Lung Chang¹, Manyam Praveen Kumar, Rai-Shung Liu

Affiliation

¹ Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan, ROC.

PMID: 15074929
DOI: 10.1021/jo0303867

Abstract

TpRuPPh(3)(CH(3)CN)(2)PF(6) catalyzed the efficient rearrangement of alpha,beta-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.