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. 2022 May 23;61(22):e202201418.
doi: 10.1002/anie.202201418. Epub 2022 Mar 31.

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

Min Han  1   2 , Shi-Qi Zhang  1 , Xin Cui  1 , Qi-Wei Wang  2   3 , Guang-Xun Li  1 , Zhuo Tang  1
Affiliations

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

Min Han et al. Angew Chem Int Ed Engl. .

Abstract

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.

Keywords: 1,4-Dihydropyridines; Axial Chirality; Bromination; Desymmetrization; Organocatalysis.

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