Polyhydroxylated indolines and oxindoles from C-glycosides via sequential Henry reaction, Michael addition, and reductive amination/amidation

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TypeArticle
Journal titleJournal of Organic Chemistry
Volume72
Issue7
Pages26862689; # of pages: 4
SubjectAmination; Canada; chemical synthesis; chemistry; Glycosides; Hydroxylation; Indoles; Magnetic Resonance Spectroscopy; Molecular Structure; Oxidation-Reduction; yield
Abstract6-nitro-2'-carbonyl-C-glycofuranosides synthesized via Henry reaction from 1-C-allyl 5-aldo-C-glycoside underwent an intramolecular Michael addition to afford nitrocyclohexanol derivatives in good to excellent yield. Reduction of the nitro group followed by intramolecular amination with ketone and aldehyde and amidation with ester produced indoline and oxindole derivatives, respectively, in excellent yield
Publication date
LanguageEnglish
AffiliationNRC Institute for Biological Sciences; National Research Council Canada
Peer reviewedNo
NRC numberZOU2007A
NPARC number9389008
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Record identifier9a4e880d-34fd-4ef3-90d5-66a1a58e259f
Record created2009-07-10
Record modified2016-05-09
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