Organocatalytic enantioselective α-difluoromethylketone thiolation of β-keto esters using phthalimide-SCF<sub>2</sub>COAr
The first asymmetric α-difluoromethylketone thiolation of diverse β-keto esters using an electrophilic phthalimide-SCF<sub>2</sub>COAr reagent (PhthN-SCF<sub>2</sub>COAr) was reported. In the presence of cinchona-alkaloid-based catalyst (DHQD)<sub>2</sub>PHAL, the reaction was achieved in moderate yields with a moderate to excellent enantioselectivity (up to 93% ee) under mild reaction conditions and exhibited functional group compatibility. An ammonium hydrogen-bonded induction model was proposed to rationalize the origin of enantioselectivity.
Authors
- Xusheng Shao (ORCID: https://orcid.org/0000-0002-2579-7533)
- Xiaoyong Xu (ORCID: https://orcid.org/0000-0001-9679-3153)
- Wu‐Lin Yang (ORCID: https://orcid.org/0000-0001-7985-5017)
- Zhong Li (ORCID: https://orcid.org/0000-0001-6665-5040)
- En Wang (ORCID: https://orcid.org/0000-0001-8302-2376)
- Junqing Liang
- Wenning Chang
Institutions
- East China University of Science and Technology (CN)
Publication Details
- Journal
- Organic & Biomolecular Chemistry
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5ob00520e
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Natural Science Foundation of China