期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 14, 页码 5660-5664出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201915870
关键词
[4]helicenes; asymmetric catalysis; Au catalysis; enantioselective synthesis; ligand design
资金
- Deutsche Forschungsgemeinschaft [AL 1348/8-1, INST 186/1237-1, INST 186/1324-1]
A highly enantioselective synthesis of 1,12-disubstituted [4]carbohelicenes is reported. The key step for the developed synthetic route is a Au-catalyzed intramolecular alkyne hydroarylation, which is achieved with good to excellent regio- and enantioselectivity by employing TADDOL-derived (TADDOL=alpha,alpha,alpha,alpha-tetraaryl-1,3-dioxolane-4,5-dimethanol) alpha-cationic phosphonites as ancillary ligands. Moreover, an appropriate design of the substrate makes the assembly of [4]helicenes of different substitution patterns possible, thus demonstrating the synthetic utility of the method. The absolute stereochemistry of the newly prepared structures was determined by X-ray crystallography and characterization of their photophysical properties is also reported.
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