80377-01-1Relevant academic research and scientific papers
Nucleophilic acylation of esters by acid chlorides mediated by samarium diiodide: Formation and use of samarium enediolates.
Machrouhi, Fouzia,Namy, Jean-Louis,Kagan, Henri B.
, p. 7183 - 7186 (2007/10/03)
Acid chlorides react with esters in the presence of samarium diiodide and catalytic amounts of NiI2 to afford samarium enediolates which can further react with electrophiles such as water or aldehydes to give respectively α-ketols or α-dihydroxyketones.
Samarium Diiodide in Tetrahydropyran: Preparation and some Reactions in Organic Chemistry.
Namy, Jean-Louis,Colomb, Marielle,Kagan, Henri B.
, p. 1723 - 1726 (2007/10/02)
SmI2 could be readily prepared in tetrahydropyran (THP) from samarium and 1,2-diiodoethane.Reducing properties were studied, showing marked differences compared to the classical SmI2/THF system.
Synthesis of α-Ketols Mediated by Divalent Samarium Compounds
Collin, Jacqueline,Namy, Jean-Louis,Dallemer, Frederic,Kagan, Henri B.
, p. 3118 - 3122 (2007/10/02)
Coupling reactions of acid chlorides are mediated by SmI2 and SmCp2, leading to α-ketols 3.Condensation reactions of acid chlorides on aldehydes similarly product α-ketols 5; with ketones, best results are obtained with use of SmI2.Reactivities of SmI2 and SmCp2 are compared and mechanisms of the reactions discussed.Formation of an acylsamarium species is shown.
α-Amino Carbanions. Preparation, Metalation, and Alkylation of Enamidines. Synthesis of Piperidine and Pyrrolidine Natural Products and Homologation of Carbonyl Compounds
Meyers, A. I.,Edwards, Philip D.,Bailey, Thomas R.,Jagdmann, G. Erik
, p. 1019 - 1026 (2007/10/02)
Saturated heterocycles, as their tert-butylformamidines, may be transformed into enamidines, by metalation-selenation-elimination.These enamidines are valuable precursors to 2-substituted, 2,4-disubstituted, and 2,4,6-trisubstituted pyrrolidines, piperidines, and perhydroazepines, prepared in a regiospecific manner.The method is demonstrated by the synthsesis of selenopsin A and the red fire ant venom.The use of acyclic enamidines is displayed as a homologation reagent which converts carbonyl compounds to higher alkyl derivatives.
