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Stereoselective construction of carbocycles and heterocycles via cascade reactions involving curcumins and nitroalkenes

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Title Stereoselective construction of carbocycles and heterocycles via cascade reactions involving curcumins and nitroalkenes
 
Creator AYYAGARI, N
JOSE, D
MOBIN, SM
NAMBOOTHIRI, INN
 
Subject DOUBLE MICHAEL REACTION
FEIST-BENARY REACTION
ORGANOCASCADE REACTIONS
BIFUNCTIONAL THIOUREA
CONJUGATE ADDITION
ANALOGS
WATER
DERIVATIVES
CANCER
DIASTEREOSELECTIVITY
Curcumin
Nitroalkene
Double Michael addition
Feist-Benary reaction
 
Description The reaction of curcumins with nitroalkenes has been investigated for the first time. Highly functionalized cyclohexanones possessing three contiguous chiral centers with complete diastereoselectivity have been synthesized through an inter-intramolecular double Michael reaction involving curcumin and nitroalkene under extremely simple experimental conditions (K(2)CO(3) in aqueous THF). Under identical conditions, curcumins react with alpha-bromonitroalkenes to afford dihydrofurans through an intermolecular Michael addition-intramolecular nucleophilic substitution (O-alkylation), which is analogous to an 'interrupted' Feist-Benary reaction. These novel transformations of curcumins empower us to expand the repertoire of curcumin based therapeutics. (C) 2010 Elsevier Ltd. All rights reserved.
 
Publisher PERGAMON-ELSEVIER SCIENCE LTD
 
Date 2012-06-26T08:40:40Z
2012-06-26T08:40:40Z
2011
 
Type Article
 
Identifier TETRAHEDRON LETTERS,52(2)258-262
0040-4039
http://dx.doi.org/10.1016/j.tetlet.2010.11.017
http://dspace.library.iitb.ac.in/jspui/handle/100/14206
 
Language English