Synthesis of axially chiral N-aryl benzimidazoles via chiral phosphoric acid catalyzed enantioselective oxidative aromatization

Given the great importance of N-substituted benzimidazoles in pharmaceutics, here N-aryl benzimidazoline produced in situ was used as a H-2 donor, which was converted to C-N axially chiral N-aryl benzimidazole by CPA-catalyzed enantioselective transfer hydrogenation of the in situ produced imine.

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Bibliographic Details
Published inNew journal of chemistry Vol. 46; no. 14; pp. 6398 - 6402
Main Authors Chen, Jin-fang, Shi, Jin-yi, Yin, Cong-cong, Cui, Xin, Li, Guang-xun, Tang, Zhuo, Zhao, Jin-zhong
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 05.04.2022
Royal Society of Chemistry
Subjects
Aromatic compounds
Chemistry
Chemistry, Multidisciplinary
Enantiomers
Phosphoric acid
Physical Sciences
Science & Technology
BRONSTED ACID
ATROPISOMERS
TRANSFER HYDROGENATION
CONSTRUCTION
COMPLEXES
HYDRIDE
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Summary:Given the great importance of N-substituted benzimidazoles in pharmaceutics, here N-aryl benzimidazoline produced in situ was used as a H-2 donor, which was converted to C-N axially chiral N-aryl benzimidazole by CPA-catalyzed enantioselective transfer hydrogenation of the in situ produced imine.
ISSN:1144-0546
1369-9261
DOI:10.1039/d1nj06092a