Bipyridine-,'-dioxides Catalysts: Design, Synthesis, and Application in Asymmetric Synthesis of 1-Pyrazolo[3,4-]pyridine Analogues.

Org Lett

School of Chemistry and Chemical Engineering/State Key Laboratory Incubation Base for Green Processing of Chemical Engineering, Shihezi University, Shihezi, Xinjiang 832003, China.

Published: May 2024


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Article Abstract

A novel type of highly efficient chiral 2-symmetric bipyridine-,'-dioxides ligand application in catalyzing Michael addition/Cyclization of 5-aminopyrazoles with α,β-unsaturated 2-acyl imidazoles has been developed, affording the corresponding adducts in 85-97% yield with up to 99% enantioselectivity under mild conditions with a lower catalyst loading and broad scope. Remarkably, this protocol exhibits advantages in terms of reactivity and enantioselectivity, giving the fact that as low as 2.2 mol % of and 2.0 mol % of Ni(OTf) can promote the title reaction on gram scale to afford the desired product with excellent enantioselectivity.

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http://dx.doi.org/10.1021/acs.orglett.4c00515DOI Listing

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