Nouf Alhamdan - Pyrolysis of azetidinone derivatives: a versatile route towards electron-rich alkenes, C-1 allylation and/or homologation of aldehydes

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      Publication Details (including relevant citation   information):

      Al-Hamdan, Nouf S., Habib, Osama M., Ibrahim, Yehia A., Al-Awadi,   Nouria A., El-Dusouqui, Osman M. E. RSC Advances  2014 4 (40) 21023-21031

      Abstract: Pyrolysis of [small beta]-lactams and   [small beta]-thiolactams led essentially to stereoselective   synthesis of the high energy electron-rich Z-alkenes. Extension   of this methodology to the pyrolysis of 3-allyloxy derivatives   gave a simple direct route to the synthetically important   4-pentenal. These pyrolytic transformations convert aldehydes to   aryloxyalkenes (a protected homologation) and 4-pentenal (a C-1   allylation and homologation). The starting 3-aryloxy and   3-allyloxy-[small beta]-lactams were synthesized by the standard   Staudinger ketene-imine [2 + 2] cycloaddition. The corresponding   [small beta]-thiolactams have readily been obtained in good   yields by thiation of [small beta]-lactams with Lawesson's   reagent.

      Address (URL): http://dx.doi.org/10.1039/C4RA01024H