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Aerobic Oxidation/Annulation Cascades through Synergistic Catalysis of RuCl 3 and N-Heterocyclic Carbenes.
Chemistry : a European Journal 2018 September 4
Cooperative catalysis combining a transition metal with an N-heterocyclic carbene is challenging due to strong binding of NHCs towards late transition metals. We report the first example of synergistic catalysis by a chiral NHC and a coordinatively unsaturated ruthenium compound. RuCl3 was found to mediate efficient aerobic oxidation of homoenolates generated from enals and the N-heterocyclic carbene. The resulting α,β-unsaturated acylazolium intermediate reacts selectively with 1,3-dicarbonyl compounds or ketones at either the β- or γ-carbon, yielding polysubstituted chiral lactones in high yield and with excellent enantioselectivity (up to 98 % yield, 94 % ee). This protocol can be applied to structurally sophisticated substrates.
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