ASYMMETRIC SYNTHESIS AND STEREOCHEMISTRY OF CHIRAL <i>cis</i>- AND <i>trans</i>-3-ALKYL-4-AMINOPIPERIDINES
DOI:
https://doi.org/10.1007/1193Keywords:
3-alkyl-4-aminopiperidines, cis isomers, trans isomers, conformational analysis, diastereomeric excess, diastereoselective synthesis, Z-E isomerism of iminesAbstract
Chiral nonracemic 3-substituted cis- and trans-4-aminopiperidines, which are precursors of anilidopiperidine analgesics, were obtained by diastereoselective synthesis from 1-methyl- and 1-benzyl-4-[(S)-1-phenylethyl]iminopiperidines, using the following reaction sequence: metalation with lithium diethylamide, alkylation with alkyl halides, and hydride reduction or hydrogenation over Raney nickel. The steric direction of the reaction, three-dimensional structure, preferred conformation, and absolute configuration of the resultant aminopiperidines were determined.
Authors: G. V. Grishina, E. R. Luk'yanenko, A. A. Borisenko, and M. Yu. Antipin.
English Translation in Chemistry of Heterocyclic Compounds, 2012, 48 (5), pp 733-747
