Switchable Chemoselectivity in [3 + 3] Annulation of β,γ-Unsaturated α-Ketoesters and 1Pyrazol-5-amines by Cooperative Acid Catalysis with Ni and In.

Org Lett

Key Laboratory of Optic-electric Sensing and Analytic Chemistry for Life Science, MOE, College of Chemistry and Molecular Engineering, Qingdao University of Science & Technology, Qingdao, Shandong 266042, China.

Published: August 2024

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 1pyrazol-5-amines in the presence of phosphoric acid , affording functionalized 1pyrazolo[3,4-]pyridines in up to 97% yields and highly enantioselective 4,5-dihydro-1-pyrazolo[3,4-]pyridines in up to 92% yield and 99% ee.

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http://dx.doi.org/10.1021/acs.orglett.4c02529DOI Listing

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