Chem Catalysis
Volume 3, Issue 6, 15 June 2023, 100594
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Review
Synthetic strategies and mechanistic studies of axially chiral styrenes

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The bigger picture

Atropisomeric styrenes are an essential category of axially chiral compounds with constrained rotation of the C(vinyl)-C(aryl) single bond, which attracts more and more attention as platform molecules convert into chiral ligands and catalysts. The recent past has witnessed rapid development of the strategy of synthesizing atropisomeric styrenes. The development of the method of synthesizing atropisomeric styrenes is summarized in this review by highlighting the mechanistic insights. Current challenges and the future orientations in this area are also supplied.

Summary

Axially chiral molecules, as a distinct subclass of molecular chirality, exist in a series of biologically active compounds and are put to use extensively in chiral ligands and catalysts. Atropisomeric styrenes are an essential category of axially chiral compounds with constrained rotation of the C(vinyl)-C(aryl) single bond, in which the less rigid framework of styrenes normally induces instability with lower rotational barriers compared with biaryl atropisomers. While lacking attention for a long time, recent advances in this category of unique structures have expanded rapidly, and plenty of means have been developed for chemical preparation of styrenes exhibiting atropisomeric optical activity. In this review, we expound on the synthetic strategies and some corresponding mechanistic studies of axially chiral styrenes, aiming to give scientists who are interested in this topic inspiration and helpful advice.

Keywords

axially chiral styrenes
synthetic strategies
mechanistic studies
DFT

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