83948-47-4Relevant 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.
Preparation of Primary Amines and 2-Azetidinones via N-Trimethylsilyl Imines
Hart, David J.,Kanai, Ken-ichi,Thomas, Dudley G.,Yang, Teng-Kuei
, p. 289 - 294 (2007/10/02)
Nonenolizable aldehydes react with lithium bis(trimethylsilyl)amide at ambient temperatures to afford solutions of N-trimethylsilyl aldimines.Treatment of these solutions with Grignard reagents or alkyllithiums followed by an aqueous workup gives primary amines in moderate to excellent yields.Treatment of N-trimethylsilyl aldimines with ester enolates provides an expedient route to 1-unsubstituted 2-azetidinones.
