4.7 Review

Recent advances in the construction of axially chiral arylpyrroles

Journal

SCIENCE CHINA-CHEMISTRY
Volume 66, Issue 9, Pages 2480-2491

Publisher

SCIENCE PRESS
DOI: 10.1007/s11426-023-1671-y

Keywords

axial chirality; pyrrole atropisomers; transition-metal catalysis; organocatalysis

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The catalytic enantioselective preparation of axially chiral molecules has become a topic of significant interest in recent decades due to their wide-ranging applications. While there are well-established synthetic approaches for six-membered axially chiral skeletons, methods for five-membered axially chiral compounds are relatively rare. Among these compounds, axially chiral arylpyrroles are particularly important and desirable. This review summarizes recent advances in the atroposelective preparation of arylpyrroles, focusing on the synthetic methods for each axially chiral framework, reaction mechanisms, and applications.
Catalytic enantioselective preparation of axially chiral molecules has gained considerable interest over the past decades, due to their numerous applications in bioactive molecules, natural products, pharmaceuticals, materials, ligands, and catalysts. Compared with the well-established synthetic approaches for six-membered axially chiral skeletons, methodologies directed towards five-membered axially chiral compounds are relatively rare. Among these, axially chiral arylpyrroles are especially important structural motifs with wide utility, and the atroposelective synthesis of them is highly desirable. In recent years, novel strategies have been developed based on transition-metal catalysis and organocatalysis. This review summarizes the recent achievements in atroposelective preparation of arylpyrroles, by emphasizing the synthetic methods for each axially chiral framework, reaction mechanisms, and applications.

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