Ruthenium-Catalyzed Formal Asymmetric Reductive Isomerization of α-Hydroxyenones
The isomerization of α-hydroxyketones (acyloins) is a fundamental transformation in carbohydrate chemistry. It has been found to play important roles in the metabolic processes of living organisms and organic synthesis. However, catalytic asymmetric acyloin isomerization remains a formidable challenge and has not been addressed. In this work, we report the unprecedented ruthenium-catalyzed formal asymmetric reductive isomerization of α-hydroxyenones. The protocol affords a variety of enantioenriched acyloins with a high level of enantioselectivities, and systematic mechanistic studies demonstrate a transformation involving the isomerization of α-hydroxyenones and ruthenium-catalyzed asymmetric transfer hydrogenation. The work provides an alternative approach to realizing the challenging catalytic asymmetric acyloin isomerization.
Authors
- Shouang Lan
- Xinqiang Fang (ORCID: https://orcid.org/0000-0001-8217-7106)
- Jinggong Liu (ORCID: https://orcid.org/0000-0001-7755-2186)
- Shuang Yang (ORCID: https://orcid.org/0000-0001-7114-5686)
- Qi Zhang (ORCID: https://orcid.org/0000-0001-6340-0130)
- Wennan Dong
- Lixuan Zhu
- Peng Luo
- Zhifei Zhao
- Caiyi Ren
Institutions
- Shihezi University (CN)
- Hefei University of Technology (CN)
- Guangdong Provincial Hospital of Traditional Chinese Medicine (CN)
- Fujian Institute of Research on the Structure of Matter (CN)
- University of Chinese Academy of Sciences (CN)
- Ministry of Industry and Information Technology (CN)
Publication Details
- Journal
- ACS Catalysis
- Published
- 2024-12-10
- DOI
- https://doi.org/10.1021/acscatal.4c05378
- Citations
- 2
- Primary Topic
- Asymmetric Hydrogenation and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 0.32
Funders
- National Natural Science Foundation of China
- Chinese Academy of Sciences
- Natural Science Foundation of Fujian Province
- Natural Science Foundation of Anhui Province