Synthesis of quaternary stereogenic centres via stereoselective intermolecular Friedel-Crafts reactions |
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| Authors: | Ball Jennifer C Gleave Robert Jones Simon |
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| Institution: | Department of Chemistry, University of Sheffield, Dainton Building, Brook Hill, Sheffield, S3 7HF, UK. |
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| Abstract: | Highly stereoselective Friedel-Crafts reactions have been performed using a chiral anthracene template to control the selectivity of the reaction. In the case of additions to fully substituted N-acyliminium ions, competitive elimination and condensation reactions were observed. Retro-Diels-Alder reaction of one of the reaction products led to a precursor that could be used for the construction of pyroglutamic acids bearing quaternary stereogenic centres. |
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