Axially chiral compounds occupy a privileged role within the field of organocatalysis. Despite this, relatively few catalytic asymmetric methods have been disclosed for their synthesis. Our research aims to develop a new catalytic asymmetric SNAr reaction for the desymmetrization of prochiral biaryl compounds. Under asymmetric phase-transfer conditions, we have demonstrated that a nucleophile is able to discriminate between two enantiotopic reactive sites. A subsequent 'proof-reading' kinetic resolution reinforces the atropselectivity within this process, leading to highly enantioenriched novel biaryl compounds.

Synthesis of axially chiral biaryls via a desymmetrizing cation directed S<sub>N</sub>Ar reaction

248th National Meeting (2014)

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Synthesis of axially chiral biaryls via a desymmetrizing cation directed SNAr reaction

Synthesis of axially chiral biaryls via a desymmetrizing cation directed S_NAr reaction