Abstract
In recent years, the synthesis of axially chiral compounds has received considerable attention due to their extensive application as biologically active compounds in medicinal chemistry and as chiral ligands in asymmetric catalysis. Chiral phosphoric acids are recognized as efficient organocatalysts for a variety of enantioselective transformations. In this review, we summarize the recent development of chiral phosphoric acid-catalyzed synthesis of a wide range of axially chiral biaryls, heterobiaryls, vinylarenes, N-arylamines, spiranes, and allenes with high efficiency and excellent stereoselectivity.
Highlights
Axial chirality is one of the most important properties of nature, resulting from the nonplanar arrangement of four groups in pairs about a chirality axis
Asymmetric synthesis of axial chiral compounds has been paid much attention [6], and great progress has been made in recent years
In 2013, Akiyama and co-workers described the enantioselective preparation of multisubstituted biaryls by the desymmetrization strategy, which was further enhanced by the subsequent asymmetric reaction in the presence of chiral phosphoric acid chiral phosphoric acids (CPAs) 3
Summary
Axial chirality is one of the most important properties of nature, resulting from the nonplanar arrangement of four groups in pairs about a chirality axis. Chiral phosphoric acids are widely used in stereoselective oxidative/ cross-coupling of two aryl counterparts, asymmetric control of aromatic ring formation, atroposelective functionalization of biaryl compounds, and so on [17,29,30] In this context, Akiyama (2004) described that chiral phosphoric acids (CPAs) have great potential for catalysis of a wide range of reactions to achieve good to perfect enantioselectivities. Chiral phosphoric acids have shown promising properties in asymmetric catalysis and play a significant catalytic role in the development of axially chiral compounds with biaryls, heterobiaryls, atropisomeric arylalkenes, allenes, and spiranes, there are only few comprehensive reviews in this area. The aim of this review is to provide readers with an overview of recent advances in the asymmetric phosphoric acidcatalyzed synthesis of axially chiral compounds and to suggest that much more attention should be paid to these catalysts in order to promote asymmetric synthesis
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