Enantiodivergent synthesis of pyrrolo[2,1-a]isoquinolines based on diastereoselective parham cyclization and alpha-amidoalkylation reactions

An enantiomerically pure N-phenethylnorborn-5-en-endo-2,3-dicarboxyimide, with a 2-exo-hydroxy-10-bornylsulfinyl group as a chiral auxiliary was used to develop an enantiodivergent synthesis of C-10b-substituted pyrrolo[2,1-a]isoquinolines. The key reactions obtained from diastereoselective parham cyclization and alpha-amidoalkylation reactions are highlighted.