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Title: Catalytic activation of carbohydrates as formaldehyde equivalents for Stetter reaction with enones
Authors: Zhang, Junmin
Xing, Chong
Tiwari, Bhoopendra
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.
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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