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We developed a novel asymmetric Friedel-Crafts alkylation/transamidation tandem reaction for the enantio- and diastereoselective synthesis of pyrazolo[3,4-b]pyridin-6-ones bearing a -CF3 unit via synergistic chiral phosphoric acid and MgSO4 catalysis. This… Click to show full abstract
We developed a novel asymmetric Friedel-Crafts alkylation/transamidation tandem reaction for the enantio- and diastereoselective synthesis of pyrazolo[3,4-b]pyridin-6-ones bearing a -CF3 unit via synergistic chiral phosphoric acid and MgSO4 catalysis. This [3 + 3] annulation protocol allows the formation of trifluoromethylated pyrazolo[3,4-b]pyridin-6-ones with two adjacent tertiary stereocenters in moderate to high yields (up to 90%), enantioselectivities (up to 97% ee), and diastereoselectivities (up to >20:1 dr).
Journal Title: Organic letters
Year Published: 2022
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