Nickel-Catalyzed One-Pot H/D Exchange and Asymmetric Michael Addition in the Presence of D<sub>2</sub>O
A step-economical and efficient strategy for the enantioselective synthesis of tetradeuterated γ-nitroketones using a cost-effective and readily available deuterium source is highly desirable. Herein, we report a nickel-catalyzed one-pot H/D exchange and highly enantioselective Michael addition of α,β-unsaturated 2-acyl imidazoles with nitromethane in the presence of D<sub>2</sub>O. This protocol demonstrates excellent efficiency, high enantioselectivity, and a broad substrate scope, offering a practical and versatile approach to accessing deuterium-labeled compounds.
Authors
- Dong Zhang (ORCID: https://orcid.org/0000-0002-3020-3218)
- Biao Xia (ORCID: https://orcid.org/0000-0002-0761-1870)
- Hui Zhou (ORCID: https://orcid.org/0000-0001-7018-3277)
- Haoting Wang
- Yuxiang Zhang (ORCID: https://orcid.org/0000-0002-0174-3514)
- Jie Ruan (ORCID: https://orcid.org/0000-0003-0168-3619)
- Jing Zhou (ORCID: https://orcid.org/0000-0003-1237-3296)
- Yan Min
- Junyu Zhou
Institutions
- The Affiliated Yongchuan Hospital of Chongqing Medical University (CN)
- Chongqing Medical and Pharmaceutical College (CN)
- Chongqing Medical University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-03-24
- DOI
- https://doi.org/10.1021/acs.joc.4c02860
- Primary Topic
- Chemical Reactions and Isotopes
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Natural Science Foundation of China
- Chongqing Medical University
- Natural Science Foundation of Chongqing
- Chongqing Municipal Education Commission