Copper-Catalyzed Enantioselective (3 + 3) Cycloaddition of Ethynyl Methylene Cyclic Carbamates with <i>N</i>,<i>N′</i>-Cyclic Azomethine Imines
A copper-catalyzed asymmetric cross 1,3-dipolar cycloaddition between 2-aminoallyl zwitterions generated <i>in situ</i> from ethynyl methylene cyclic carbamates and <i>N</i>,<i>N'</i>-cyclic azomethine imines has been realized. The reaction, which utilizes a commercially available chiral tridentate <i>N</i>-ligand, delivers a range of functionally rich chiral hexahydro-8<i>H</i>-pyrazolo[1,2-<i>a</i>][1,2,4]triazin-8-one derivatives in 51-99% yields with good to high enantioselectivities (44-95% ee).
Authors
- Xiang‐Ping Hu (ORCID: https://orcid.org/0000-0002-8214-1338)
- Yahui Li (ORCID: https://orcid.org/0000-0002-3779-4911)
Institutions
- Dalian Institute of Chemical Physics (CN)
- Chinese Academy of Sciences (CN)
- University of Chinese Academy of Sciences (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-04-16
- DOI
- https://doi.org/10.1021/acs.orglett.5c01114
- Citations
- 5
- Primary Topic
- Synthesis and Catalytic Reactions
- Type
- article
- Field-Weighted Citation Impact
- 4.68
Funders
- National Natural Science Foundation of China
- Dalian Institute of Chemical Physics