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An Asymmetric Aromatic Finkelstein Reaction: A Platform for Remote Diarylmethane Desymmetrization.
- Source :
-
Journal of the American Chemical Society [J Am Chem Soc] 2023 Oct 18; Vol. 145 (41), pp. 22322-22328. Date of Electronic Publication: 2023 Oct 03. - Publication Year :
- 2023
-
Abstract
- A first-of-its-kind enantioselective aromatic Finkelstein reaction is disclosed for the remote desymmetrization of diarylmethanes. The reaction operates through a copper-catalyzed C-I bond-forming event, and high levels of enantioselectivity are achieved through the deployment of a tailored guanidinylated peptide ligand. Strategic use of transition-metal-mediated reactions enables the chemoselective modification of the aryl iodide products; thus, the synthesis of a diverse set of otherwise difficult-to-access diarylmethanes with excellent levels of selectivity is realized from a common intermediate. A mixed experimental/computational analysis of steric parameters and substrate conformations identifies the importance of remote conformational effects as a key to achieving high enantioselectivity in this desymmetrization reaction.
Details
- Language :
- English
- ISSN :
- 1520-5126
- Volume :
- 145
- Issue :
- 41
- Database :
- MEDLINE
- Journal :
- Journal of the American Chemical Society
- Publication Type :
- Academic Journal
- Accession number :
- 37788150
- Full Text :
- https://doi.org/10.1021/jacs.3c08727