Atroposelective Synthesis of Axially Chiral N‐Arylpyrroles by Chiral‐at‐Rhodium Catalysis

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Abstract: A transformation of fluxional into configurationally stable axially chiral N‐arylpyrroles was achieved with a highly atroposelective electrophilic aromatic substitution catalyzed by a chiral‐at‐metal rhodium Lewis acid. Specifically, N‐arylpyrroles were alkylated with N‐acryloyl‐1H‐pyrazole electrophiles in up to 93 % yield and with up to >99.5 % ee, and follow‐up conversions reveal the synthetic utility of this new method. DFT calculations elucidate the origins of the observed excellent atroposelectivity.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Atroposelective Synthesis of Axially Chiral N‐Arylpyrroles by Chiral‐at‐Rhodium Catalysis ; volume:59 ; number:32 ; year:2020 ; pages:13552-13556 ; extent:5
Angewandte Chemie / International edition. International edition ; 59, Heft 32 (2020), 13552-13556 (gesamt 5)

Creator: Ye, Chen‐Xi
Chen, Shuming
Han, Feng
Xie, Xiulan
Ivlev, Sergei
Houk, Kendall N.
Meggers, Eric

DOI: 10.1002/anie.202004799

URN: urn:nbn:de:101:1-2022061112522121462082

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

Last update: 15.08.2025, 7:28 AM CEST

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Associated

Ye, Chen‐Xi
Chen, Shuming
Han, Feng
Xie, Xiulan
Ivlev, Sergei
Houk, Kendall N.
Meggers, Eric

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