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Synlett 1996; 1996(6): 582-584
DOI: 10.1055/s-1996-5469
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Stereoselective Synthesis of Aminoalkyl-Substituted β-Lactams via Cycloaddition of Ketenes Generated from α-Amino Acids

Joachim Podlech*
  • *Institut für Organische Chemie und Isotopenforschung der Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany, Telefax: Int. code +711 / 685 4321; E-mail: joachim.podlech@po.uni-stuttgart.de
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Publication Date:
31 December 2000 (online)

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Photochemical rearrangement of diazoketones 1-8 (derived from suitably protected α-amino acids) in the presence of imines led to the diastereoselective formation of aminoalkyl-substituted β-lactams 10-17. The two diastereoisomeric trans-substituted ring systems were formed with selectivities up to 93:7 and yields up to 90 %.

β-lactams - Wolff rearrangement - ketenes - β-amino acid derivatives

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