Journal
TETRAHEDRON LETTERS
Volume 52, Issue 2, Pages 258-262Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.11.017
Keywords
Curcumin; Nitroalkene; Double Michael addition; Feist-Benary reaction
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Funding
- DST India
- UGC India
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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 (K2CO3 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.
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