Chiral Phosphoric Acid Catalyzed Enantioselective Desymmetrization of 1,4-Dihydropyridines by C(sp3 )-H Bromination.

Min Han, Shi-Qi Zhang, Xin Cui, Qi-Wei Wang, Guang-Xun Li, Zhuo Tang

Angewandte Chemie (International ed. in English) 2022 May 23

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Described herein is the enantioselective synthesis of Hantzsch-type 1,4-dihydropyridines (DHPs), which are frequently contained in pharmaceuticals. Readily available symmetrical 1,4-DHPs were used as substrates, and the methyl group at the 2- or 6-position of the 1,4-DHP was selectively monobrominated by desymmetrizing enantioselective bromination. The inert C-H bond was converted into a versatile C-Br bond, which guaranteed the modification of the chiral 1,4-DHP derivatives with high efficiency. Furthermore, axially chiral 4-aryl pyridines were accessible by central-to-axial chirality conversion. © 2022 Wiley-VCH GmbH.

Citation

Min Han, Shi-Qi Zhang, Xin Cui, Qi-Wei Wang, Guang-Xun Li, Zhuo Tang. Chiral Phosphoric Acid Catalyzed Enantioselective Desymmetrization of 1,4-Dihydropyridines by C(sp3 )-H Bromination. Angewandte Chemie (International ed. in English). 2022 May 23;61(22):e202201418