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Stereo- and Chemodivergent NHC-Promoted Functionalisation of Arylalkylketenes with Chloral
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Douglas, James J., Churchill, Gwydion, Slawin, Alexandra M. Z., Fox, David J. and Smith, Andrew D. (2015) Stereo- and Chemodivergent NHC-Promoted Functionalisation of Arylalkylketenes with Chloral. Chemistry - A European Journal, 21 (46). pp. 16354-16358. doi:10.1002/chem.201503308 ISSN 0947-6539.
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Official URL: http://dx.doi.org/10.1002/chem.201503308
Abstract
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.
Item Type: | Journal Article | ||||
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Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||
Journal or Publication Title: | Chemistry - A European Journal | ||||
Publisher: | Wiley - V C H Verlag GmbH & Co. KGaA | ||||
ISSN: | 0947-6539 | ||||
Official Date: | November 2015 | ||||
Dates: |
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Volume: | 21 | ||||
Number: | 46 | ||||
Page Range: | pp. 16354-16358 | ||||
DOI: | 10.1002/chem.201503308 | ||||
Status: | Peer Reviewed | ||||
Publication Status: | Published |
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