Switchable Chemoselectivity in [3 + 3] Annulation of β,γ-Unsaturated α-Ketoesters and 1<i>H-</i>Pyrazol-5-amines by Cooperative Acid Catalysis with Ni<sup>II</sup> and In<sup>I</sup>
The exchange of the metal ion from Ni(II) to In(I) leads to a switch in the chemoselectivity of the [3 + 3] annulation of β,γ-unsaturated α-ketoesters and 1<i>H-</i>pyrazol-5-amines in the presence of phosphoric acid <b>1</b>, affording functionalized 1<i>H-</i>pyrazolo[3,4-<i>b</i>]pyridines <b>4</b> in up to 97% yields and highly enantioselective 4,5-dihydro-1<i>H</i>-pyrazolo[3,4-<i>b</i>]pyridines <b>5</b> in up to 92% yield and 99% ee.
Authors
- Songyang Li
- Chenxi Guo (ORCID: https://orcid.org/0000-0002-8908-7258)
- Mengdie Tang
- Ran Song
- Daoshan Yang
- Jian Lv (ORCID: https://orcid.org/0000-0001-7641-5411)
- Man Wang (ORCID: https://orcid.org/0000-0001-7190-4582)
Institutions
- Qingdao University of Science and Technology (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-08-05
- DOI
- https://doi.org/10.1021/acs.orglett.4c02529
- Citations
- 5
- Primary Topic
- Asymmetric Synthesis and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 1.25
Funders
- Natural Science Foundation of Shandong Province
- Qingdao University of Science and Technology
- Taishan Scholar Project of Shandong Province
- Natural Science Fund for Distinguished Young Scholars of Shandong Province