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Synthesis 1995; 1995(1): 83-86
DOI: 10.1055/s-1995-3846
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2-Dibenzylaminobutane-1,4-diol: An Effective Chiral Building Block for the Synthesis of 1,2-Amino Alcohols

Peter Gmeiner* , Annerose Kärtner
  • *Pharmazeutisches Institut der Universität Bonn, An der Immenburg 4, 53121 Bonn, Germany
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Publication Date:
31 December 2000 (online)

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Regioselective activation and protection of the chiral building block 1, readily available from L-aspartic acid, leads to the key intermediate 8. Employing classical nucleophiles, heterocyclic anions or organocuprates, 8 could be transformed into the displacement products 9. Finally, hydrolysis affords the homochiral 1,2-amino alcohols 4 in 48-77% yield (based on 8).

A general chiral pool synthesis of 1,2-amino alcohols of type 4 is reported.