Stereoselective synthesis of pyrano[2,3- <i>c</i> ]pyrazolone derivatives <i>via</i> light-induced NHC catalyzed [4 + 2] annulations
Herein, chiral pyrano[2,3-<i>c</i>]pyrazolone derivatives bearing vicinal tertiary and quaternary carbon stereocenters have been synthesized <i>via</i> light-induced N-heterocyclic carbene (NHC) catalyzed asymmetric [4 + 2] cycloaddition of 4-arylidenylpyrazolones and α-diazoketones in moderate to good yields with good enantio- and diastereoselectivities (24 examples, up to 93% yield, 95% ee and >20 : 1 dr). This protocol features mild reaction conditions, high efficiency, and broad substrate scope.
Authors
- Changsheng Yao (ORCID: https://orcid.org/0000-0002-0185-2366)
- Jiaomei Wang
- Kai Zhang (ORCID: https://orcid.org/0000-0001-9341-0444)
- Xian Li
- Yao Chen (ORCID: https://orcid.org/0000-0003-2008-2691)
- Chenxia Yu
- Siyan Miao
Institutions
- Jiangsu Normal University (CN)
- Xuzhou University of Technology (CN)
Publication Details
- Journal
- Organic & Biomolecular Chemistry
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5ob00586h
- Citations
- 1
- Primary Topic
- N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- National Natural Science Foundation of China
- Jiangsu Normal University
- Natural Science Foundation of Jiangsu Province
- Basic Research Program of Jiangsu Province