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Synthesis 1999; 1999(4): 650-654
DOI: 10.1055/s-1999-3440
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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
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Publication Date:
31 December 1999 (online)

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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

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