126017-85-4Relevant academic research and scientific papers
N -Acyliminium Ion Chemistry: Improving the Access to Unsaturated γ-Lactams and Their N -α-Methoxylated Derivatives: Application to an Expeditive Synthesis of (±)-Crispine A
Drici, Wassila,Fayssal, Sandra Abi,Lazouni, Imane,Pérard-Viret, Jo?lle,Souquet, Florence,Thueillon, Sébastien
, p. 2970 - 2978 (2020/10/18)
An improved synthesis of unsaturated γ-lactams by condensation of various primary amines with 2,5-dimethoxy-2,5-dihydrofuran is described. A modified mechanism for this reaction is suggested. Synthesis of their N -α-methoxylated derivatives, as N -acyliminium ion precursors, is also reported. Finally, a short synthesis of (±)-crispine A is presented as an illustrative application.
Asymmetric induction α to nitrogen in pyrrolidines and piperidines via radical chemistry
Ewin, Richard A.,Jones, Keith,Newton, Christopher G.
, p. 1107 - 1111 (2007/10/03)
Attempts to control the stereochemistry of radical reactions at the 2-position of pyrrolidines and piperidines carrying chiral auxiliaries on the nitrogen are presented.
Enantioselective Total Synthesis of Indolizidine Alkaloids (-)-205A and (-)-235B
Polniaszek, Richard P.,Belmont, Stephen E.
, p. 4868 - 4874 (2007/10/02)
Enantioselective total syntheses of indolizidine alkaloids (-)-205A and (-)-235B are described.The syntheses proceed via a common late-stage intermediate, α-aminonitrile 1.Absolute stereochemical control over the C8 and C8a stereocenters in these material
Enantioselective Total Syntheses of Indolizidine Alkaloids 167B and 209D
Polniaszek, Richard P.,Belmont, Stephen E.
, p. 4688 - 4693 (2007/10/02)
Enantioselective total syntheses of the indolizidine alkaloids 167B and 209D are described.The sytheses proceed via a common late-stage intermediate, amino nitrile 8.Each alkaloid was prepared in 10 steps and approximately 23percent overall yield from (S)
Stereoselective Nucleophilic Additions to the Carbon-Nitrogen Double Bond. 3. Chiral Acyliminium Ions
Polniaszek, Richard P.,Belmont, Stephen E.,Alvarez, Ramon
, p. 215 - 223 (2007/10/02)
(S)-(-)-α-Phenethylamine (3), (S)-(-)-1-(2-chlorophenyl)ethylamine (4), (S)-(-)-1-(2,6-dichlorophenyl)ethylamine (5), and (S)-(-)-1-(2,3,4,5,6-pentachlorophenyl)ethylamine (6) have been incorporated into acyliminium ions of structural type 1 and 2.Five-me
