Enantioselective Nucleophilic Vinylic Substitution of Nitroolefins for the Synthesis of 3-Alkenyl Oxindoles
An asymmetric catalytic nucleophilic vinylic substitution (S<sub>N</sub>V) reaction of 5<i>H</i>-thiazol-4-ones and nitroolefins has been developed for the synthesis of 3-alkenyl oxindoles. The enantioselective S<sub>N</sub>V reaction with a nitro group as the leaving group proceeded smoothly to afford 3-alkenyl oxindoles in good yields with high regio- and enantioselectivity. The reaction showed broad substrate applicability. A quaternary carbon stereocenter, which was substituted by sp<sup>2</sup> carbon, was constructed under mild reaction conditions.
Authors
- Zhenyu Shi (ORCID: https://orcid.org/0000-0001-7428-0832)
- Weiwu Ren (ORCID: https://orcid.org/0000-0002-9485-1679)
- Yuan Pan (ORCID: https://orcid.org/0000-0002-2284-236X)
- Pan Zhou (ORCID: https://orcid.org/0000-0001-9496-8810)
- Kaihong Qi
Institutions
- Qingdao National Laboratory for Marine Science and Technology (CN)
- Ocean University of China (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-05-08
- DOI
- https://doi.org/10.1021/acs.joc.5c00190
- Citations
- 2
- Primary Topic
- Asymmetric Synthesis and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 1.87
Funders
- National Natural Science Foundation of China
- Natural Science Foundation of Shandong Province
- Taishan Scholar Project of Shandong Province
- Fundamental Research Funds for the Central Universities