Ranganathappa, SS and Dehury, BS and Singh, GK and Shee, S and Biju, AT (2024) Atroposelective Synthesis of N-N Axially Chiral Indoles and Pyrroles via NHC-Catalyzed Diastereoselective (3 + 3) Annulation Strategy. In: ACS Catalysis . pp. 6965-6972.
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Abstract
The synthesis of N-N axially chiral molecules in the enantiopure form has emerged as an interesting research topic primarily due to the significance and intricacy in synthesizing these molecules, especially bearing heterocyclic motifs. Herein, we disclose a method for the introduction of N-N axial chirality along with a point chiral center via the N-heterocyclic carbene (NHC)-catalyzed atroposelective synthesis of dihydropyridinone-containing indoles and pyrroles. The reaction follows a (3 + 3) annulation approach by the interception of indole/pyrrole-derived enamines with α,β-unsaturated aldehydes under oxidative NHC catalysis proceeding via the α,β-unsaturated acylazoliums. The N-N axially chiral indoles/pyrroles were formed under mild conditions in broad scope with high selectivity. In addition, preliminary DFT studies of the N-N rotational barrier of the axially chiral products were performed. © 2024 American Chemical Society.
| Item Type: | Journal Article |
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| Publication: | ACS Catalysis |
| Publisher: | American Chemical Society |
| Additional Information: | The copyright for this article belongs to authors. |
| Department/Centre: | Division of Chemical Sciences > Organic Chemistry |
| Date Deposited: | 24 May 2024 04:50 |
| Last Modified: | 24 May 2024 04:50 |
| URI: | https://eprints.iisc.ac.in/id/eprint/85058 |
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