Diastereoselective Construction of Bridged Azabicyclo[3.2.1]octane via Copper-Catalyzed Formal [4 + 3] Cycloaddition
A novel copper-catalyzed formal diastereoselective [4 + 3] cycloaddition of 2-arylaziridines and 2-substituted cyclopentadiene was developed. This transformation provided an efficient protocol for the assembly of a highly strained bridged azabicyclo[3.2.1]octane scaffold, which is widespread in bioactive natural products. A likely mechanism showed that the reaction proceeds through [3 + 2] cycloaddition, ring opening, and aza-Michael addition cascade reaction. This protocol features high efficiency and diastereoselectivity, wide functional group compatibility, and a cheap catalyst.
Authors
- Qing‐Bao Zhang (ORCID: https://orcid.org/0000-0002-8778-1318)
- Tzu‐Rong Peng (ORCID: https://orcid.org/0000-0002-0754-5682)
- Xu Yan (ORCID: https://orcid.org/0000-0002-3138-5578)
- Fang Wang (ORCID: https://orcid.org/0000-0001-5200-4175)
- Yang Yang (ORCID: https://orcid.org/0000-0001-8142-3571)
- Yulong He (ORCID: https://orcid.org/0000-0002-2043-3896)
Institutions
- Wuhan University (CN)
- Weifang University of Science and Technology (CN)
- Renmin Hospital of Wuhan University (CN)
- Huazhong University of Science and Technology (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-12-31
- DOI
- https://doi.org/10.1021/acs.joc.4c02801
- Primary Topic
- Synthesis and Catalytic Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Natural Science Foundation of China
- Huazhong University of Science and Technology