Synthesis of 3-propargyl isoindolinones by Pd/Cu-catalyzed enantioselective Heck/Sonogashira reaction of enamides
Herein, we report an enantioselective Pd/Cu-catalyzed sequential Heck/Sonogashira coupling reaction of electron-rich enamides with terminal alkynes as substrates. This transformation proceeds smoothly to afford 3-propargyl isoindolinone derivatives bearing quaternary stereogenic centers in moderate to good yields (43-77% yield) and good to excellent enantioselectivity (up to 93% ee). Functional groups such as halogen atoms (F, Cl, and Br), thienyl, and silyl moieties are tolerated well. Synthetic transformations of the 3-propargyl isoindolinone product show the utility value of the reaction.
Authors
- Yi‐Xia Jia (ORCID: https://orcid.org/0000-0001-7936-0049)
- Ying Pan (ORCID: https://orcid.org/0000-0001-8613-8817)
- Ren‐Xiao Liang (ORCID: https://orcid.org/0000-0003-0931-1975)
- Qiang Wang (ORCID: https://orcid.org/0000-0003-1935-2631)
- Yu Lin Hu (ORCID: https://orcid.org/0000-0003-2139-5032)
Institutions
- Tianjin University of Technology (CN)
- Chinese Academy of Sciences (CN)
- Shanghai Institute of Organic Chemistry (CN)
- Zhejiang University of Technology (CN)
Publication Details
- Journal
- Organic & Biomolecular Chemistry
- Published
- 2024-12-10
- DOI
- https://doi.org/10.1039/d4ob01881h
- Citations
- 3
- Primary Topic
- Synthesis and pharmacology of benzodiazepine derivatives
- Type
- article
- Field-Weighted Citation Impact
- 0.75
Funders
- National Natural Science Foundation of China
- Natural Science Foundation of Zhejiang Province