Catalytic Enantioselective Synthesis of Atropisomeric Biaryls: A Cation‐Directed Nucleophilic Aromatic Substitution Reaction |
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Authors: | Roly J Armstrong Prof?Dr Martin D Smith |
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Institution: | Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA (UK) http://msmith.chem.ox.ac.uk/ |
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Abstract: | 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. |
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Keywords: | aromatic substitution atropisomerism chirality kinetic resolution phase‐transfer catalysis |
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