The first highly enantioselective asymmetric Friedel-Crafts reaction/Cyclization reaction of 5-amino pyrazole with 3-alkenyl-oxindole to afford polycyclic heterocyclic compound bearing an all-carbon quaternary stereocenter catalyzed by NiII-C2-symmetric bipyridine-N,N'-dioxides ligands has been developed. The relevant products with a wide range of substrates and good functional tolerance were obtained in 89-98% yields with 56-99% enantioselectivities in the presence of in the presence of 11 mol % of L1 and 10 mol % of Ni(OTf)2 in DCM at room temperature. In addition, a scale-up experiment and the synthetic transformations of the cycloadducts further highlighted the synthetic utility.
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Tong et al. (2024) studied this question.
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