Chiral Phosphoric Acid-Catalyzed Kinetic Resolution of Tertiary Alcohol-Tethered Ynamides via Controllable Hydroalkoxylation
Catalytic kinetic resolution has proven to be a powerful and practical method for the preparation of enantioenriched tertiary alcohols since their racemates are easy to access. However, this strategy is highly challenging and generally relies on transition-metal catalysis and is mostly limited to the construction of five- and six-membered O-heterocycles. Herein, we disclose an efficient and controllable kinetic resolution of tertiary alcohol-tethered ynamides enabled by chiral phosphoric acid catalysis, which represents a unique chiral Brønsted acid-catalyzed alkyne functionalization via kinetic resolution of tertiary alcohols. This metal-free protocol allows the practical and atom-economic formation of chiral medium-sized N-heterocycles such as nine-membered lactams and benzoxazepines with high enantioselectivities.
Authors
- Xin Hong (ORCID: https://orcid.org/0000-0003-4717-2814)
- Long‐Wu Ye (ORCID: https://orcid.org/0000-0003-3108-2611)
- Cai‐Ming Wang
- Hongxing Zheng (ORCID: https://orcid.org/0000-0001-6033-5126)
- Gan-Lu Qian
- Da-Qiu Cui
- Ye-Nan Yang
- Bo Zhou (ORCID: https://orcid.org/0000-0002-5551-678X)
Institutions
- Xiamen University (CN)
- Chinese Academy of Sciences (CN)
- Nankai University (CN)
- Shanghai Institute of Organic Chemistry (CN)
- Clean Energy (United States) (US)
- State Key Laboratory of Chemical Engineering (CN)
- State Key Laboratory of Clean Energy Utilization
- Zhejiang University (CN)
Publication Details
- Journal
- ACS Catalysis
- Published
- 2025-01-27
- DOI
- https://doi.org/10.1021/acscatal.4c08055
- Citations
- 5
- Primary Topic
- Catalytic Alkyne Reactions
- Type
- article
- Field-Weighted Citation Impact
- 4.68
Funders
- Henan Normal University
- National Natural Science Foundation of China
- Chinese Academy of Sciences
- State Key Laboratory of Clean Energy Utilization
- State Key Laboratory of Physical Chemistry of Solid Surfaces, Xiamen University
- National Key Research and Development Program of China
- Fundamental Research Funds for the Central Universities
- Science and Technology Department of Zhejiang Province
- Beijing National Laboratory for Molecular Sciences
- Natural Science Foundation of Zhejiang Province