PDF herunterladen
Synthesis 1999; 1999(4): 650-654
DOI: 10.1055/s-1999-3440
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

A Chiral, Oxidatively Cleavable Auxiliary in β-Lactam Synthesis - Double Diastereocontrol with p-Methoxyphenethyl-Substituted Imines

Joachim Podlech* , Steffen Steurer
  • *Institut für Organische Chemie der Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany; Fax +49(7 11)6 85 42 69; E-mail: joachim-podlech@po.uni-stuttgart.de
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
31. Dezember 1999 (online)

  als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik

A new chiral, oxidatively removable auxiliary for the Staudinger reaction is presented. When diazo ketones 1-3 prepared from suitably protected amino acids reacted with p-methoxyphenethyl (PMPE)-substituted imines, the corresponding trans-substituted β-lactams 7 and 8a-h were formed. With the (S)-configured imine 5, an improvement of the selectivities is observed in comparison with achiral p-methoxybenzyl (PMB)-substituted imines by double stereoselection; consequently, the ratio of isomers decreased with the (R)-imine 4. The auxiliary could be removed with cerium ammonium nitrate (CAN).

protecting groups - double stereoinduction - β-lactam synthesis - diazo ketones - imines