Russian Journal of Organic Chemistry

, Volume 41, Issue 6, pp 807–810 | Cite as

A Simple Diastereoselective Synthesis of Chiral Nonracemic Aliphatic Amines

  • G. V. Grishina
  • E. R. Luk’yanenko
  • A. A. Borisenko


An efficient procedure has been developed for the diastereoselective synthesis of chiral aliphatic amines (diastereoisomeric excess >96%) from (1S)-N-(1-methylethylidene)-1-phenylethylamine, i.e., Schiff base derived from the simplest ketone (acetone) and (1S)-1-phenylethylamine. The procedure includes successive lithiation, alkylation, and reduction and is characterized by high regioselectivity in the formation of alkylated syn-Z-imines. Hydride reduction of the prochiral C=N bond in the latter gives mainly optically active aliphatic amines with R configuration. All reactions are performed as a one-pot process without isolation of intermediate products.


Acetone Organic Chemistry Ketone Hydride Alkylation 


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Copyright information

© MAIK “Nauka/Interperiodica” 2005

Authors and Affiliations

  • G. V. Grishina
    • 1
  • E. R. Luk’yanenko
    • 1
  • A. A. Borisenko
    • 1
  1. 1.Faculty of ChemistryLomonosov Moscow State UniversityMoscowRussia

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