An Unusual Chemoselective Cycloaddition of Nonstabilized Azomethine Ylide: Synthesis of Oxazolidine Derivatives
An unusual [3 + 2] cycloaddition involving nonstabilized azomethine ylides and unsaturated carbonyl compounds is reported, wherein the reaction exclusively occurs at the carbonyl group rather than the conjugated double bond. This annulation strategy enables the efficient synthesis of a diverse range of substituted oxazolidine frameworks with excellent yields (up to 96%) under mild reaction conditions. Control experiments suggest that the unexpected selectivity likely arises from the electron-withdrawing ester group adjacent to the carbonyl, which enhances its reactivity.
Authors
- Jian Hua Yang (ORCID: https://orcid.org/0000-0002-6401-276X)
- Yushuang Chen (ORCID: https://orcid.org/0000-0003-4157-8709)
- Bowen Hu (ORCID: https://orcid.org/0000-0001-9815-8938)
- Xiang Gao (ORCID: https://orcid.org/0000-0002-3774-1852)
- Yulong Zhang
- Xiang Zhong Ren (ORCID: https://orcid.org/0000-0002-4321-4282)
- Jiahao Xu (ORCID: https://orcid.org/0009-0006-8410-2371)
- Xiaolin Li (ORCID: https://orcid.org/0009-0003-5801-7737)
Institutions
- Chongqing Normal University (CN)
- Chongqing University of Science and Technology (CN)
- Sichuan Center for Disease Control and Prevention (CN)
Publication Details
- Journal
- Chemistry - An Asian Journal
- Published
- 2025-10-26
- DOI
- https://doi.org/10.1002/asia.70392
- Primary Topic
- Synthesis and Catalytic Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Natural Science Foundation of China
- Chongqing University
- Chongqing Municipal Education Commission
- Chongqing University of Science and Technology