Atropisomeric amides: stereoselective enolate chemistry and enantioselective synthesis via a new SmI2-mediated reduction

The use of certain types of atropisomeric amides, incorporating an N-MEM-ortho-tert-butylaniline group, for stereoselective reactions, has been explored. Enolate reactions of these systems are highly diastereocontrolled, and enantiomerically enriched starting materials can be obtained, starting from lactic acid, via a new SmI2 mediated reduction process.