78428-90-7Relevant academic research and scientific papers
N-Trimethylsilyl Imines: Applications to the Synthesis of β-Lactams
Ha, Deok-Chan,Hart, David J.,Yang, Teng-Kuei
, p. 4819 - 4825 (2007/10/02)
Ester enolates and N-trimethylsilyl imines react to afford N-protio-β-lactams.The stereochemical course of the reaction depends on the ester enolate geometry.Therefore (E)-enolates give mainly cis β-lactams while (Z)-enolates give nearly equal mixtures of cis and trans β-lactams.The use of ethyl β-hydroxybutyrate as the ester component allows the preparation of β-lactams of potential use in carbapenem synthesis.The differences in the behavior of N-trimethylsilyl and N-aryl imines in ester-imine condensations are also discussed.
New Synthetic Route for the Preparation of 4-Phenylthio-4-butanolide Derivatives by the Use of the Pummerer Rearrangement
Watanabe, Mikio,Nakamori, Seijin,Hasegawa, Hatsue,Shirai, Kozo,Kumamoto, Takanobu
, p. 817 - 821 (2007/10/02)
The Pummerer rearrangement reaction of 2- or 3-substituted 4-(phenylsulfinyl)butyric acids in the presence of an excess amount of acetic anhydride and a catalytic amount of p-toluenesulfonic acid in refluxing toluene for 1 h afforded 2- or 3-substituted 4-phenylthio-4-butanolide (17a-f).Thermolysis in pyridine of 4-phenylsulfinyl 4-butanolides, which were prepared by oxidation of 17a-f, afforded 2- or 3-substituted 2- or 3-buten-4-olides.
