Ayyagari, Narasimham ; Jose, Deena ; Mobin, Shaikh M. ; Namboothiri, Irishi N.N. (2011) Stereoselective construction of carbocycles and heterocycles via cascade reactions involving curcumins and nitroalkenes Tetrahedron Letters, 52 (2). pp. 258-262. ISSN 0040-4039
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Official URL: http://doi.org/10.1016/j.tetlet.2010.11.017
Related URL: http://dx.doi.org/10.1016/j.tetlet.2010.11.017
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 (K2CO 3 in aqueous THF). Under identical conditions, curcumins react with α-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.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 121569 |
| Deposited On: | 19 Jul 2021 09:55 |
| Last Modified: | 19 Jul 2021 09:55 |
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