Stereoselective Nickel-Catalyzed Iterative 1,2-Reduction of Trisubstituted Enones to Cycloalkanols Bearing Two Contiguous Stereocenters
Herein we first report a nickel-catalyzed asymmetric iterative 1,2-reduction of trisubstituted enones to cycloalkanols with two contiguous stereocenters in high yields with excellent diastereo- and enantioselectivities (36 examples, up to 98.5:1.5 er, >20:1 dr, TON = 500). The combined experimental and computational mechanistic studies suggested energy changes during two consecutive reduction processes and provided a range of unique mechanistic rationales that have not been disclosed in nickel-catalyzed asymmetric hydrogenation-related studies.
Authors
- Cheng Hou (ORCID: https://orcid.org/0000-0003-2967-0326)
- Xumu Zhang (ORCID: https://orcid.org/0000-0001-5700-0608)
- Qixing Liu (ORCID: https://orcid.org/0000-0001-6102-1321)
- Haifeng Zhou (ORCID: https://orcid.org/0000-0002-8850-585X)
- Congcong Yin
- Chaoxin Yang (ORCID: https://orcid.org/0000-0002-5573-8606)
- Linhong Zuo
- Yue Liu (ORCID: https://orcid.org/0000-0001-7657-392X)
Institutions
- China Three Gorges University (CN)
- Guangxi Normal University (CN)
- Southern University of Science and Technology (CN)
- Green Chemistry (PL)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-04-14
- DOI
- https://doi.org/10.1021/acs.orglett.5c00839
- Citations
- 4
- Primary Topic
- Asymmetric Hydrogenation and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 2.15
Funders
- Natural Science Foundation of Yichang City
- National Natural Science Foundation of China
- Natural Science Foundation of Hubei Province
- Higher Education Discipline Innovation Project