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

Abstract

AbstractUtilization 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.