Construction of Dihydropyrano[2,3‐<i>c</i>]pyrazolone via Photo‐induced Wolff Rearrangement/Chiral Isothiourea Catalyzed [4+2] Cyclization Reaction
Abstract A photoinduced Wolff rearrangement/chiral isothiourea catalyzed [4+2] cycloaddition reaction of pyrazolone derivatives and α ‐diazoketones was developed, affording the corresponding dihydropyrano[2,3‐ c ]pyrazolone derivatives in moderate to good yields (50–94 %) with satisfactory to excellent diastereoselectivities (>20 : 1 dr, in almost all cases) and enantioselectivities of 31–99 %. This protocol features readily available substrates, mild reaction conditions, and effective construction of vicinal tertiary and quaternary carbon stereocenters.
Authors
- Wenjin Yan
- Siyu Shi (ORCID: https://orcid.org/0000-0001-9010-7431)
- Xia Liu (ORCID: https://orcid.org/0000-0002-3110-9602)
- Jinqi Huang (ORCID: https://orcid.org/0000-0002-5961-6841)
- Zhiqiang Shen (ORCID: https://orcid.org/0000-0003-0804-2478)
- Hai Guo
- Zhou Zhang
Institutions
- Guangdong Medical College (CN)
- Chinese Academy of Sciences (CN)
- Lanzhou Institute of Chemical Physics (CN)
- Lanzhou Institute of Husbandry and Pharmaceutical Sciences (CN)
- Guangzhou First People's Hospital (CN)
- Lanzhou University Second Hospital (CN)
- Affiliated Hospital of Guangdong Medical College Hospital (CN)
- State Key Laboratory of Oxo Synthesis and Selective Oxidation (CN)
- Lanzhou University (CN)
- South China University of Technology (CN)
- Guangzhou Medical University (CN)
Publication Details
- Journal
- Asian Journal of Organic Chemistry
- Published
- 2024-08-13
- DOI
- https://doi.org/10.1002/ajoc.202400387
- Citations
- 4
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 1.00
Funders
- National Natural Science Foundation of China
- Basic and Applied Basic Research Foundation of Guangdong Province