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Enantioselective Synthesis of Inherently Chiral Calix[4]arenes via Palladium-Catalyzed Asymmetric Intramolecular C–H Arylations
- Source :
- Journal of the American Chemical Society. 144:22858-22864
- Publication Year :
- 2022
- Publisher :
- American Chemical Society (ACS), 2022.
-
Abstract
- We report herein an efficient approach for the enantioselective synthesis of inherently chiral calix[4]arenes via palladium-catalyzed asymmetric intramolecular C-H arylations. Using a chiral bifunctional phosphine-carboxylate ligand, the inherent chirality on macrocyclic scaffolds was induced successfully, from which a wide range of calix[4]arenes with fluorenone motifs were obtained with good yields and excellent enantioselectivities (up to99% ee). The synthetic utility of this method was demonstrated by diverse transformations of the products, thus substantially expanding the chemical space of chiral calix[4]arenes. Further investigations of photophysical and chiroptical properties revealed that calix[4]arenes bearing two fluorenone moieties displayed remarkable
- Subjects :
- Colloid and Surface Chemistry
General Chemistry
Biochemistry
Catalysis
Subjects
Details
- ISSN :
- 15205126 and 00027863
- Volume :
- 144
- Database :
- OpenAIRE
- Journal :
- Journal of the American Chemical Society
- Accession number :
- edsair.doi.dedup.....69652879f8bcd05c85bf443763aa6100