197173-13-0Relevant academic research and scientific papers
Preparation of imides via the palladium-catalyzed coupling reaction of organoborons with methyl N -[methoxy(methylthio)methylene]carbamate as a one-carbon elongation reaction
Tomizawa, Takuhei,Orimoto, Kohei,Niwa, Takashi,Nakada, Masahisa
supporting information, p. 6294 - 6297 (2013/02/23)
The preparation of imides via the palladium-catalyzed coupling reaction as a one-carbon elongation reaction is described. The palladium-catalyzed coupling reaction of aryl-, alkyl-, and alkenylborons with N-[methoxy(methylthio) methylene]carbamate in the presence of Cu(I) thiophene-2-carboxylate (CuTC) affords imino ethers that are converted to the corresponding imides by acidic hydrolysis in high yield. The imino ethers are also useful for preparing the corresponding ester without using carbon monoxide.
The preparation and intra- and intermolecular addition reactions of acyclic N-acylimines: Application to the synthesis of (±)-sertraline
DeNinno,Eller,Etienne
, p. 6988 - 6993 (2007/10/03)
Intramolecular endo-cyclization reactions of N-acyliminium ions have seen wide application for the synthesis of heterocyclic compounds. The corresponding exocyclic variant, which would provide 1-aminotetralin derivatives, for example, has little precedent. We have discovered that acyclic N-acylcarbamates can be readily reduced to the corresponding N-acylhemiaminal derivatives in high yield using DIBAL as the reducing agent. These intermediates are remarkably stable and, if desired, can be purified and stored. The acyclic N-acylhemiaminals undergo both intra- and intermolecular nucleophilic addition reactions mediated by strong Lewis acids, such as TiCl4. Diastereoselectivity, induced either by a substituent on the newly formed ring, or by utilizing a chiral ester on the carbamic acid, was disappointingly low. This methodology was successfully applied to the synthesis of the racemic form of the marketed antidepressant sertraline.
