Enantioselective Total Synthesis of (−)‐Finerenone Using Asymmetric Transfer Hydrogenation

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Abstract: (−)‐Finerenone is a nonsteroidal mineralocorticoid receptor antagonist currently in phase III clinical trials for the treatment of chronic kidney disease in type 2 diabetes. It contains an unusual dihydronaphthyridine core. We report a 6‐step synthesis of (−)‐finerenone, which features an enantioselective partial transfer hydrogenation of a naphthyridine using a chiral phosphoric acid catalyst with a Hantzsch ester. The process is complicated by the fact that the naphthyridine exists as a mixture of two atropisomers that react at different rates and with different selectivities. The intrinsic kinetic resolution was converted into a kinetic dynamic resolution at elevated temperature, which enabled us to obtain (−)‐finerenone in both high yield and high enantioselectivity. DFT calculations have revealed the origin of selectivity.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Enantioselective Total Synthesis of (−)‐Finerenone Using Asymmetric Transfer Hydrogenation ; volume:59 ; number:51 ; year:2020 ; pages:23107-23111 ; extent:5
Angewandte Chemie / International edition. International edition ; 59, Heft 51 (2020), 23107-23111 (gesamt 5)

Creator: Lerchen, Andreas
Gandhamsetty, Narasimhulu
Farrar, Elliot H. E.
Winter, Nils
Platzek, Johannes
Grayson, Matthew N.
Aggarwal, Varinder K.

DOI: 10.1002/anie.202011256

URN: urn:nbn:de:101:1-2022061112313561079527

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:30 AM CEST

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Associated

Lerchen, Andreas
Gandhamsetty, Narasimhulu
Farrar, Elliot H. E.
Winter, Nils
Platzek, Johannes
Grayson, Matthew N.
Aggarwal, Varinder K.

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Enantioselective Total Synthesis of (−)‐Finerenone Using Asymmetric Transfer Hydrogenation

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Other Objects (12)

Enantioselective Total Synthesis of (−)‐Finerenone Using Asymmetric Transfer Hydrogenation

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Ruthenium-Catalyzed Enantioselective Transfer Hydrogenation

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Asymmetric Ruthenium-Catalyzed Transfer Hydrogenation of Ketones

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