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|Title:||Catalytic activation of carbohydrates as formaldehyde equivalents for Stetter reaction with enones||Authors:||Zhang, Junmin
Chi, Robin Yonggui
|Keywords:||DRNTU::Science::Chemistry||Issue Date:||2013||Source:||Zhang, J., Xing, C., Tiwari, B., & Chi, Y. R. (2013). Catalytic Activation of Carbohydrates as Formaldehyde Equivalents for Stetter Reaction with Enones. Journal of the American Chemical Society, 135(22), 8113–8116.||Series/Report no.:||Journal of the American Chemical Society||Abstract:||We disclose the first catalytic activation of carbohydrates as formaldehyde equivalents to generate acyl anions as one-carbon nucleophilic units for a Stetter reaction. The activation involves N-heterocyclic carbene (NHC)-catalyzed C–C bond cleavage of carbohydrates via a retro-benzoin-type process to generate the acyl anion intermediates. This Stetter reaction constitutes the first success in generating formal formaldehyde-derived acyl anions as one-carbon nucleophiles for non-self-benzoin processes. The renewable nature of carbohydrates, accessible from biomass, further highlights the practical potential of this fundamentally interesting catalytic activation.||URI:||https://hdl.handle.net/10356/104155
|ISSN:||0002-7863||DOI:||10.1021/ja401511r||Rights:||© 2013 American Chemical Society.||Fulltext Permission:||none||Fulltext Availability:||No Fulltext|
|Appears in Collections:||SPMS Journal Articles|
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