Asymmetric synthesis of 5-arylmethylpyrrolidin-2-ones and 2-arylmethylpyrrolidines

Article abstract of DOI:10.1016/S0957-4166(03)00589-5

An efficient methodology for the enantioselective synthesis of 5-arylmethylpyrrolidin-2-ones and 2-arylmethylpyrrolidines has been devised. The key step is the stereoselective hydrogenation of the N-acylhydrazonium salts obtained from the corresponding arylmethylene hydrazides. These highly conjugated compounds are readily prepared by reacting a chiral succinimide with a variety of arylmethyl Grignard reagents. Removal of the chiral auxiliary and subsequent reduction complete the synthesis of the title compounds.