Yb(<scp>OTf</scp>)<sub>3</sub>‐Catalyzed Asymmetric [3+3] Cycloaddition of <i>N</i>‐Vinyl Nitrones with Activated Cyclopropanes to Prepare 1,2‐Oxazines
Comprehensive Summary We described a Yb(OTf) 3 combined with Pybox ligand catalyzed asymmetric [3+3] cycloaddition of N ‐vinyl cinnamaldehyde nitrones with activated cyclopropanes to prepare various functionalized 1,2‐oxazines in 24%—95% yields and 22%—96% ee. Experimental results revealed that the reaction underwent a domino [3+3] cycloaddition, dealkenylation, and aza‐1,4‐addition in three steps. The chiral 1,2‐oxazine could be obtained in gram scales and easily converted into various 1,2‐oxazine scaffolds. The present method features broad substrate scope, good functional group compatibility, three‐component domino reaction, and asymmetric [3+3] cycloaddition of N ‐vinyl nitrones with activated cyclopropanes.
Authors
- Samuel J. Huang (ORCID: https://orcid.org/0000-0002-8464-8503)
- Dong‐Liang Mo (ORCID: https://orcid.org/0000-0002-4005-2249)
- Yixin Chen (ORCID: https://orcid.org/0000-0003-0206-7279)
- Chunhua Chen (ORCID: https://orcid.org/0000-0001-9589-6329)
- Yu‐Zheng Wu
- Ning Zou (ORCID: https://orcid.org/0000-0001-7438-7197)
- Yue Leng
Institutions
- State Ethnic Affairs Commission (CN)
- Guangxi Normal University (CN)
- Neijiang Normal University (CN)
Publication Details
- Journal
- Chinese Journal of Chemistry
- Published
- 2024-11-25
- DOI
- https://doi.org/10.1002/cjoc.202400937
- Citations
- 12
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 3.00
Funders
- Natural Science Foundation of Guangxi Zhuang Autonomous Region
- National Natural Science Foundation of China
- Natural Science Foundation of Sichuan Province