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Conjugate addition of curcumins to chalcones and azodicarboxylates

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Title Conjugate addition of curcumins to chalcones and azodicarboxylates
 
Creator AYYAGARI, N
MEHTA, A
GOPI, E
DEB, I
MOBIN, SM
NAMBOOTHIRI, INN
 
Subject Michael addition
Curcumins
Chalcones
Azodicarboxylates
ELECTROPHILIC ALPHA-AMINATION
CHIRAL PALLADIUM COMPLEXES
DOUBLE MICHAEL ADDITION
ALPHA,BETA-UNSATURATED KETONES
STEREOSELECTIVE-SYNTHESIS
BETA-KETOESTERS
AMINO-ACIDS
FUNCTIONALIZED CYCLOHEXANONES
ENANTIOSELECTIVE SYNTHESIS
ASYMMETRIC-SYNTHESIS
 
Description Cascade double Michael reaction of curcumins with chalcones in the presence of Cs2CO3 in CH3CN provided highly functionalized cyclohexanones in moderate to good yields (35-77%) and good to excellent diastereoselectivities (81:19 to 95:05). Similar reaction of curcumins with azodicarboxylates in the presence of DMAP in CH3CN stopped at the single Michael addition stage affording novel hydrazinodicarboxylates of curcumins in good to excellent yields (65-85%). (C) 2013 Elsevier Ltd. All rights reserved.
 
Publisher PERGAMON-ELSEVIER SCIENCE LTD
 
Date 2014-10-17T05:29:20Z
2014-10-17T05:29:20Z
2013
 
Type Article
 
Identifier TETRAHEDRON, 69(29)5973-5980
http://dx.doi.org/10.1016/j.tet.2013.04.083
http://dspace.library.iitb.ac.in/jspui/handle/100/16069
 
Language en