Stereo- and chemodivergent NHC-promoted functionalisation of arylalkylketenes with chloral
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Stereo- and chemodivergent enantioselective reaction pathways are observed upon treatment of alkylarylketenes and trichloroacetaldehyde (chloral) with N-heterocyclic carbenes, giving selectively either β-lactones (up to 88:12 dr, up to 94 % ee) or α-chloroesters (up to 94 % ee). Either 2-arylsubstitution or an α-branched iPr alkyl substituent within the ketene favours the chlorination pathway, allowing chloral to be used as an electrophilic chlorinating reagent in asymmetric catalysis.
Douglas , J , Churchill , G , Slawin , A M Z , Fox , D J & Smith , A D 2015 , ' Stereo- and chemodivergent NHC-promoted functionalisation of arylalkylketenes with chloral ' , Chemistry - A European Journal , vol. 21 , no. 46 , pp. 16354–16358 . https://doi.org/10.1002/chem.201503308
Chemistry - A European Journal
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