Utilization of Industrial Waste Materials, 6. Utilization of Derivatives of the Bicyclic Proline Analog (<i>all‐R</i>)‐Octahydrocyclopenta[<i>b</i>]pyrrol‐2‐carboxylic Acid in the Stereoselective Synthesis

Abstract

Abstract Utilization of the industrial waste material benzyl ( all‐R )‐cyclopenta[ b ]pyrrol‐2‐carboxylate 1a or its derivatives 1b, 1c as chiral auxiliaries is described. Allylation of nitrothioacetamides, proceeding by initial S ‐allylation followed by a facile thio Claisen rearrangement, is accomplished with a diastereomeric ratio ( dr ) up to 85:15 using 1a , b as auxiliaries in stoichiometric amounts. Another aspect of this report is the diastereoselective synthesis of optically active amines, starting from aldehydes, with optical purities ( op ) up to 99%, Again a derivative of 1a was used as source of chirality.