Enantioselective Synthesis of Atropisomeric Amides by Dynamic Resolution: Thermodynamic Control with a Proline-Derived Diamine Resolving Agent.
By exploiting the thermal instability about the Ar-CO axis at high temperature, atropisomeric amides can be dynamically resolved to provide material with up to 96.5 % ee in 70-80 % overall yield from racemic starting material. The amides are coupled with a diamine resolving agent and equilibrated to single diastereoisomers. Hydrolysis returns enantiomerically enriched amide (see reaction scheme).
Clayden
JP
Department of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL (UK).
Lai
LW