Synlett 1994; 1994(10): 795-797
DOI: 10.1055/s-1994-23008
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Enantioselective Synthesis of Homoallylamines and ß-Amino acids via Nucleophilic Allylation of SAMP/RAMP-Hydrazones

Dieter Enders* , Jürgen Schankat, Martin Klatt
  • *Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, 52074 Aachen, Germany
Further Information

Publication History

Publication Date:
22 March 2002 (online)

Nucleophilic 1,2-addition of an allyl cerium reagent in THF or allyl Grignard reagent in toluene to aldehyde SAMP/RAMP-hydrazones leads to protected homoallylamines and homoallylamino acetals in good yields and high enantiomeric excesses (ee = 90-98%). Subsequent ozonolysis of the double bond and the acetal group affords ß-amino acids and diacids of high enantiomeric purity (ee = 91-93%).