Refernces
10.1021/ja00390a052
The research focuses on the synthesis and investigation of tetrahydropyridinium salts and their subsequent fragmentation to form specific diene compounds, with the ultimate goal of synthesizing (9Z,12E)-tetradecadien-1-yl acetate, a compound identical to an authentic sample. The study also explores the behavior of N-oxides in comparison to previous fragmentation processes and reports the first example of a specific type of elimination reaction. Key chemicals used in the process include tetrahydropyridinium salt 8, CsF, acetonitrile, ammonium salt 10, tetrahydropyridine 5, Grignard reagent 12, lithium tetrachlorocuprate, TsOH, MeOH, Ac20, pyridine, and various other reagents and solvents. The conclusions drawn from the research highlight the stereoselective fragmentation leading to the desired diene compounds and the establishment of the Z,Z configuration of the double bonds through NMR analysis. The study also discusses the potential applications of the synthesized compounds in the synthesis of pheromones and other natural products.
10.1016/S0040-4039(00)73963-3
This research aims to develop methods for synthesizing enantioenriched tetrahydropyridines, which are important nitrogen heterocycles found in various alkaloids and pharmacologically active agents. The study explores the use of iminium ion-vinylsilane cyclizations, focusing on amino acid-derived 4-silyl-3-alkenylamines as starting materials. Key chemicals used include L-alanine, benzaldehyde, benzamide, and various reagents for iminium ion generation such as para-toluenesulfonic acid, trifluoroacetic acid, and silver tetrafluoroborate. The researchers examined different methods for forming iminium ions and their effects on the stereochemical outcomes of the cyclizations. They found that under optimal conditions, tetrahydropyridine products with enantiomeric purities of 85-99% could be obtained. The study concludes that cyclization is more rapid than racemization, and oxidative cyclization of α-silylmethyl precursors allows for the formation of tetrahydropyridines at room temperature under neutral conditions.
10.1016/j.tetlet.2017.05.067
The study presents an efficient method for the one-pot multicomponent synthesis of highly functionalized tetrahydropyridines using graphene oxide as a carbocatalyst. The chemicals used in the study include β-ketoesters, aldehydes, and anilines, which are the reactants in the synthesis process. Graphene oxide serves as a versatile and eco-friendly catalyst, facilitating the reaction and yielding the desired tetrahydropyridine products with good to excellent yields. The study highlights the operational simplicity, use of readily available starting materials, easy work-up, and the reusability of the graphene oxide catalyst, making it an attractive approach in the context of green chemistry.