Copper-Catalyzed [2,3]-Sigmatropic Rearrangement of Azide–Ynamides via Selenium Ylides
A copper-catalyzed [2,3]-sigmatropic rearrangement of azide-ynamides via selenium ylides is disclosed, which leads to the practical and divergent synthesis of a variety of tricyclic heterocycles bearing a quaternary carbon stereocenter in generally moderate to excellent yields. Significantly, this method represents the first [2,3]-sigmatropic rearrangement of the selenium ylide based on alkynes and an unprecedented [2,3]-sigmatropic rearrangement via α-imino copper carbenes.
Authors
- Chong‐Yang Shi
- Long‐Wu Ye (ORCID: https://orcid.org/0000-0003-3108-2611)
- Sang Xiong (ORCID: https://orcid.org/0000-0003-2375-5767)
- Xin‐Qi Zhu (ORCID: https://orcid.org/0000-0003-3261-4595)
- Zhenkang Ai (ORCID: https://orcid.org/0009-0007-1382-5959)
- Xuan Wang (ORCID: https://orcid.org/0009-0003-2355-636X)
- Xin Liu (ORCID: https://orcid.org/0000-0001-8877-8420)
- Bo Zhou (ORCID: https://orcid.org/0000-0002-5551-678X)
Institutions
- Yunnan Normal University (CN)
- Xiamen University (CN)
- Chinese Academy of Sciences (CN)
- Shanghai Institute of Organic Chemistry (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-12-23
- DOI
- https://doi.org/10.1021/acs.orglett.4c04444
- Citations
- 2
- Primary Topic
- Catalytic Alkyne Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.50
Funders
- National Natural Science Foundation of China
- Yunnan Normal University