Asymmetric Synthesis of Polycyclic Heterocyclic Compounds via Friedel–Crafts Reaction/Cyclization Reaction Catalyzed by Nickel Catalyst
The first highly enantioselective asymmetric Friedel-Crafts reaction/cyclization reaction of 5-aminopyrazoles with 3-alkenyloxindoles to afford polycyclic heterocyclic compounds bearing an all-carbon quaternary stereocenter catalyzed by a complex of Ni<sup>II</sup> with the <i>C</i><sub>2</sub>-symmetric bipyridine-<i>N</i>,<i>N</i>'-dioxide ligand <b>L</b><sub><b>12</b></sub> has been developed. The relevant products with a wide range of substrates and good functional tolerance were obtained in 89-98% yield with 56-99% ee in the presence of 10 mol % Ni(OTf)<sub>2</sub> and 11 mol % <b>L</b><sub><b>12</b></sub> in DCM at 25 °C. Moreover, an experiment on scaling up the process along with the transformations of the cycloadducts further emphasized the practical application of the synthesis.
Authors
- Liangjian Hu
- Shiwu Li (ORCID: https://orcid.org/0000-0003-0699-0140)
- Zhifei Zhao
- Shujun Tong
Institutions
- Shihezi University (CN)
- Centre National de la Recherche Scientifique (FR)
- Université Paris-Saclay (FR)
- Institut de Chimie Moléculaire et des Matériaux d'Orsay (FR)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-11-11
- DOI
- https://doi.org/10.1021/acs.orglett.4c03674
- Citations
- 6
- Primary Topic
- Asymmetric Synthesis and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 1.50
Funders
- National Natural Science Foundation of China