Pyrolysis of azetidinone derivatives: A versatile route towards electron-rich alkenes, C-1 allylation and/or homologation of aldehydes
Pyrolysis of β-lactams and β-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-β-lactams were synthesized by the standard Staudinger ketene-imine [2 + 2] cycloaddition. The corresponding β-thiolactams have readily been obtained in good yields by thiation of β-lactams with Lawesson's reagent. This journal is the Partner Organisations 2014.
Al-Hamdan, Nouf S.,Habib, Osama M.,Ibrahim, Yehia A.,Al-Awadi, Nouria A.,El-Dusouqui, Osman M. E.
p. 21023 - 21031
(2014/06/09)
Mild Copper(I) iodide/β-keto ester catalyzed coupling reactions of styryl bromides with phenols, thiophenols, and imidazoles
An efficient and mild vinylation of O-, S-, and N-nucleophiles is reported. Copper(I) iodide/ethyl 2-oxocyclohexanecarboxylate is used as the catalytic system. The protocol tolerates a broad range of functional groups on the substrates, and gives the corr
Bao, Weiliang,Liu, Yunyun,Lv, Xin
experimental part
p. 1911 - 1917
(2009/04/04)
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