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Synthesis 1991; 1991(10): 829-831
DOI: 10.1055/s-1991-26583
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The Directed Cleavage of Substituted 1-Phenylethylamines: A Novel Route to Enantiomerically Pure ß-Amino Acid Esters and ß-Lactams

Gerhard Bringmann* , Torsten Geuder
  • *Institut für Organische Chemie der Universität Wurzburg, Am Hubland, D-8700 Würzburg, Germany
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Publication Date:
29 April 2002 (online)

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An efficient novel access to enantiomerically pure ß-amino acid esters and ß-lactams (e.g., methyl (3S,4S)-1-(tert-butyldimethylsilyl-4-methyl-2-oxoazetidine-3-carboxylate) from optically active 1-arylethylamines is described. Regiospecific cleavage is performed by Birch reduction and subsequent ozonolysis.