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

Abstract

Pyrolysis of b-lactams and b-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-b-lactams were synthesized by the standard

Facile Synthesis of β-Lactam Derivatives by the Staudinger Reaction Using 3,6-Dichlorotetrazine

“…TLC was carried out on silica gel 254 analytical sheets obtained from Fluka. Spectral data for 4a-c have been previously reported [23][24][25] and β-lactams 4d-l and 6a-b are new compounds.…”