Organocatalyzed asymmetric [2+2] cycloaddition of saccharin-derived endocyclic ketimines and allenoates for the synthesis of fused azetidines
We report a novel enantioselective [2 + 2] cycloaddition of allenoate and endocyclic ketimine derived from saccharin, catalyzed by a chiral tertiary amine. The methodology enables the synthesis of fused tricyclic azetidines with a quaternary stereogenic center, exhibiting high enantioselectivity and efficiency. The broad range of substrates demonstrate the generality of the protocol, and the resulting functional products can be easily converted into a variety of valuable synthons such as thiazepine derivatives.
Authors
- Dehai Li (ORCID: https://orcid.org/0000-0002-7191-2002)
- De Wang (ORCID: https://orcid.org/0000-0002-3737-6621)
- Yunfeng Zhang (ORCID: https://orcid.org/0000-0001-6928-1742)
- Luning Zhou (ORCID: https://orcid.org/0000-0001-5283-4769)
- Xinyu Liu (ORCID: https://orcid.org/0009-0001-7100-0580)
Institutions
- Qingdao National Laboratory for Marine Science and Technology (CN)
- Marine Biomedical Research Institute of Qingdao (CN)
- Ocean University of China (CN)
Publication Details
- Journal
- Tetrahedron Chem
- Published
- 2025-05-10
- DOI
- https://doi.org/10.1016/j.tchem.2025.100133
- Primary Topic
- Synthesis and Catalytic Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Natural Science Foundation of Shandong Province
- Fundamental Research Funds for the Central Universities