Palladium-Catalyzed Enantioselective Ring-Opening/Cyanation of Cyclobutanones
Palladium-catalyzed asymmetric transformations involving cyanide anions remain a challenge due to the strong affinity between cyanide anions and palladium, which induces alterations in the coordination sphere of the palladium center. Herein, palladium-catalyzed enantioselective cyanation is achieved via a ring-opening/cross-coupling process between aryl halide-tethered cyclobutanones and Zn(CN)<sub>2</sub>. This reaction is demonstrated to exhibit broad substrate scope and robust enantioselectivity. The synthetic utility is highlighted by converting the product into amide, carboxylic acid, and ester without racemization.
Authors
- Jie Yang (ORCID: https://orcid.org/0000-0001-8877-1683)
- Zheng‐Hui Guan (ORCID: https://orcid.org/0000-0003-4901-5951)
- Ming Chen (ORCID: https://orcid.org/0000-0001-9670-1239)
- Gang Wang (ORCID: https://orcid.org/0000-0003-3964-8296)
- Zhi‐Hui Ren (ORCID: https://orcid.org/0009-0007-9040-3450)
- Yi-Chuan Zhong
Institutions
- Ministry of Education of the People's Republic of China (CN)
- Department of Chemistry and Material Sciences (RU)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-04-09
- DOI
- https://doi.org/10.1021/acs.orglett.5c00979
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Natural Science Foundation of China