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Armstrong, Roly J.; Smith, Martin D.
Angewandte Chemie, November 17, 2014, Volume: 53, Issue: 47Journal Article
A catalytic enantioselective nucleophilic aromatic substitution reaction which yields axially chiral biaryl derivatives in excellent yields with e.r. values of up to 97:3 has been developed. This process uses a chiral counterion to direct the addition of thiophenolate to a prochiral dichloropyrimidine by a tandem desymmetrization/kinetic resolution mechanism. The products can be derivatized to a range of atropisomeric structures without any reduction in enantioenrichment, thus offering access to unexplored chiral biaryl architectures. Asymm‐Desymm: A catalytic asymmetric nucleophilic aromatic substitution reaction which yields axially chiral biaryls in excellent yields with e.r. values of up to 97:3 has been developed. This process uses a chiral counterion to direct the addition of thiophenolate to an achiral dichloropyrimidine by a tandem desymmetrization/kinetic resolution mechanism. The products can be derivatized, thus offering access to unexplored chiral biaryl architectures.
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