Catalytic activation of carbohydrates as formaldehyde equivalents for Stetter reaction with enones.

Content Provider	Semantic Scholar
Author	Zhang, Junmin Xing, Chong Tiwari, Bhoopendra Chi, Yonggui Robin
Copyright Year	2013
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.
Starting Page	186
Ending Page	200
Page Count	15
File Format	PDF HTM / HTML
Alternate Webpage(s)	http://www3.ntu.edu.sg/home/robinchi/publication%20lists/39%20pdf.pdf
PubMed reference number	23688031v1
Alternate Webpage(s)	https://doi.org/10.1021/ja401511r
DOI	10.1021/ja401511r
Journal	Journal of the American Chemical Society
Volume Number	135
Issue Number	22
Language	English
Access Restriction	Open
Subject Keyword	Anions Bridged Bicyclo Compounds, Heterocyclic Carbohydrate nutrients Equivalent Weight Formaldehyde Leukemoid Reaction benzoin resin carbene
Content Type	Text
Resource Type	Article