Asymmetric Cycloaddition Reactions of Aryne Intermediates with a Chiral Carbon-Carbon Axis: Syntheses of Axially Chiral Biaryl Compounds

An asymmetric synthesis via an axially chiral arylaryne intermediate was developed. A cycloaddition reaction with various arynophiles was used to obtain chiral biaryl compounds while preserving the enantiomeric excess (ee) of a precursor even though the reaction proceeds through an arylaryne intermediate, whose ee decreases on a time-dependent basis. High chiral transfer from a precursor to a product was observed not only at low temperature (-78 degrees C) but also at room temperature.

Automated summary

An asymmetric synthesis method using an axially chiral arylaryne intermediate has been developed, which allows for the formation of chiral biaryl compounds while preserving the enantiomeric excess (ee) of the precursor. The high chiral transfer from precursor to product was observed at both low and room temperature.