Sc-Catalyzed Asymmetric [2 + 2] Annulation of 2-Alkynylnaphthols with Dienes to Access Cyclobutene Frameworks
Herein, we introduce a scandium-catalyzed synthetic strategy that provides access to a diverse and functionalized array of cyclobutene frameworks adorned with a quaternary carbon center. This approach broadens the synthetic repertoire of 2-alkynylnaphthols with alkenes, offering a versatile platform for the construction of complex molecular architectures. The asymmetric catalytic [2 + 2] cycloaddition reaction demonstrates a wide substrate scope and an impressive functional group tolerance, yielding products with high efficiency, up to 97% yield, and excellent enantiomeric excess of up to 97%. The simplicity of scaling up this process, coupled with the ease of converting these cyclobutene frameworks into a variety of substituted products, significantly enhances the synthetic utility of this method.
Authors
- Cheng Peng
- Yan‐Ling Ji
- Gu Zhan (ORCID: https://orcid.org/0000-0002-5263-8263)
- Bo Han (ORCID: https://orcid.org/0000-0003-3200-4682)
- Ke Xu (ORCID: https://orcid.org/0000-0002-5465-3301)
- Heping Li (ORCID: https://orcid.org/0000-0002-4281-2475)
- Qian‐Qian Yang (ORCID: https://orcid.org/0000-0002-2682-146X)
Institutions
- Chengdu University of Traditional Chinese Medicine (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-01-16
- DOI
- https://doi.org/10.1021/acs.orglett.4c04625
- Citations
- 1
- Primary Topic
- Asymmetric Synthesis and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- National Natural Science Foundation of China
- Department of Science and Technology of Sichuan Province
- Chengdu University of Traditional Chinese Medicine