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|Title: ||Stereoselective construction of carbocycles and heterocycles via cascade reactions involving curcumins and nitroalkenes|
|Authors: ||AYYAGARI, N|
|Keywords: ||DOUBLE MICHAEL REACTION|
|Issue Date: ||2011|
|Publisher: ||PERGAMON-ELSEVIER SCIENCE LTD|
|Citation: ||TETRAHEDRON LETTERS,52(2)258-262|
|Abstract: ||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.|
|Appears in Collections:||Article|
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