Ru-catalysed oxidative cyclisation of 1,5-dienes: an unprecedented role for the co-oxidant.

ABSTRACT: The Ru-mediated oxidative cyclisation of 1,5-dienes to furnish 2,5-dihydroxyalkyl-substituted tetrahydrofuran-diols (THF-diols) represents a practical approach for the synthesis of many bioactive natural products. In the current study, we reported profound findings obtained by density functional theory (DFT) simulations, and they were consistent with the experimental conditions. The results set out a catalytic cycle within intermediacy of NaIO₄-complexed Ru(vi) species. Importantly, the co-oxidant played a critical role in the cyclisation step and subsequently the release of THF-diols. Following the formation of Ru(vi) glycolate, cyclisation and THF-diol release proceeded through NaIO₄-coordinated Ru(vi) intermediates, outpacing the Ru(viii) glycolate or THF-diolate i

SUBMITTER: Hussein AA 

PROVIDER: S-EPMC9052297 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature