Issue 16, 2022

Catalytically atroposelective ring-opening of configurationally labile compounds to access axially chiral biaryls

Abstract

Axially chiral biaryl scaffolds are vital in natural products, pharmaceuticals, and asymmetric synthesis. Catalytically atroposelective ring-opening of configurationally labile compounds, pioneered by Bringmann, has received continuous attention in the past few years, becoming one of the most unique and powerful strategies to construct axially chiral biaryls. Biaryl lactones and lactams, cyclic diaryliodonium salts, dinaphthothiophenes, diarylsulfonium salts, diarylfurans, five-membered silafluorenes and 9-aryl-9H-fluoren-9-ols are identified as representative successful skeletons. These configurationally labile compounds feature a strained cyclic structure which significantly improved their reactivity in catalytic transformations compared to the corresponding non-cyclic structures. In this minireview, we evaluate and summarize the progress in this field, and briefly state our personal perspectives on the future advancement of this direction.

Graphical abstract: Catalytically atroposelective ring-opening of configurationally labile compounds to access axially chiral biaryls

Article information

Article type
Review Article
Submitted
12 Jūn. 2022
Accepted
11 Jūl. 2022
First published
14 Jūl. 2022

Org. Chem. Front., 2022,9, 4507-4521

Catalytically atroposelective ring-opening of configurationally labile compounds to access axially chiral biaryls

G. Wang, J. Huang, J. Zhang and Z. Fu, Org. Chem. Front., 2022, 9, 4507 DOI: 10.1039/D2QO00946C

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