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 . DOI: 10.1002/chem.201503308
Chemistry - A European Journal
© 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co.KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
DescriptionFunding: UK Engineering and Physical Sciences Research Council EP/G501742/1
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