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A One-Pot, Copper-Catalyzed Cascade Route to 2-Indolyl-C-glycosides

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Title A One-Pot, Copper-Catalyzed Cascade Route to 2-Indolyl-C-glycosides
 
Creator SUBRAMANIAN, P
KALIAPPAN, KP
 
Subject Carbohydrates
C-glycosides
Nitrogen heterocycles
Alkynes
Copper
Domino reactions
ALPHA-C-MANNOSYLTRYPTOPHAN
2,3-DISUBSTITUTED INDOLES
POLYSUBSTITUTED INDOLES
NUCLEOSIDE ANALOGS
SUGAR TELLURIDES
INTERNAL ALKYNES
ARYL GLYCOSIDES
1ST SYNTHESIS
CYCLIZATION
SONOGASHIRA
 
Description An efficient and high-yielding, one-pot, Cu-catalyzed synthesis of 2-indolyl-C-glycosides is delineated. The sequence involves a cascade Sonogashira type coupling and a hydroamination reaction between sugar-derived alkynes and N-tosyl-o-iodoaniline followed by removal of the N-tosyl group to provide a library of 2-indolyl-C-glycosides in moderate to excellent yields.
 
Publisher WILEY-V C H VERLAG GMBH
 
Date 2014-10-14T17:28:48Z
2014-10-14T17:28:48Z
2013
 
Type Article
 
Identifier EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (3)595-604
http://dx.doi.org/10.1002/ejoc.201201208
http://dspace.library.iitb.ac.in/jspui/handle/100/14569
 
Language en