Stereo- and chemodivergent NHC-promoted functionalisation of arylalkylketenes with chloral
View/ Open
Date
09/11/2015Author
Grant ID
EP/D061768/1
EP/K039210/1
Keywords
Metadata
Show full item recordAbstract
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.
Citation
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
Publication
Chemistry - A European Journal
Status
Peer reviewed
ISSN
0947-6539Type
Journal article
Description
Funding: UK Engineering and Physical Sciences Research Council EP/G501742/1Collections
Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.