ArticleChemistry (Weinheim an der Bergstrasse, Germany)2015
Stereo- and Chemodivergent NHC-Promoted Functionalisation of Arylalkylketenes with Chloral.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
5 citing papers in PubMed.
- De-epimerizing DyKAT of β-lactones generated by isothiourea-catalysed enantioselective [2 + 2] cycloaddition.Chemical science · 2024Article
- Enantioselective α-heterofunctionalization reactions of catalytically generated C1-Lewis base enolates.Tetrahedron chem · 2024Article
- Probing Regio- and Enantioselectivity in the Formal [2 + 2] Cycloaddition of C(1)-Alkyl Ammonium Enolates with β- and α,β-Substituted Trifluoromethylenones.The Journal of organic chemistry · 2023Article
- Catalytic enantioselective synthesis of perfluoroalkyl-substituted β-lactonesChemical science · 2019Article
- dM-Dim for Carboxylic Acid Protection.Tetrahedron letters · 2018Article
Corrections and comments
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Authors and funding
5 authors.
Funding
No grant is acknowledged in the PubMed record.
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.
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Registered trials
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