Giel, Marie-Claire, Barrow, Andrew S, Smedley, Christopher J, Lewis, William, Moses, John E (June 2021) Aminium cation-radical catalysed selective hydration of (E)-aryl enynes. Chemical Communications. ISSN 1359-7345
Abstract
The hydration of carbon-carbon triple bonds is an important and atom economic synthetic transformation. Herein, we report a mild and selective method for the catalytic Markovnikov hydration of (E)-aryl enynes to the corresponding enones, mediated through the bench-stable aminium salt, tris(4-bromophenyl)ammoniumyl hexachloroantimonate (TBPA). The chemoselective and diastereoselective method proceeds under neutral metal-free conditions, delivering excellent product yields from terminal and internal alkyne units. The synthesis of biologically important (E)-3-styrylisocoumarins, including a formal synthesis of the natural product achlisocoumarin III, demonstrates the utility of this novel transformation.
| Item Type: | Paper |
|---|---|
| Subjects: | chemistry |
| CSHL Authors: | |
| Communities: | CSHL Cancer Center Program CSHL Cancer Center Program > Gene Regulation and Inheritance Program CSHL labs > Moses lab |
| SWORD Depositor: | CSHL Elements |
| Depositing User: | CSHL Elements |
| Date: | 22 June 2021 |
| Date Deposited: | 24 Jun 2021 15:22 |
| Last Modified: | 13 Feb 2024 16:55 |
| PMCID: | PMC8895482 |
| Related URLs: | |
| URI: | https://repository.cshl.edu/id/eprint/40227 |
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