17244-80-3Relevant academic research and scientific papers
Towards phase-transfer catalysts with a chiral anion: Inducing asymmetry in the reactions of cations
Carter, Christabel,Fletcher, Sarah,Nelson, Adam
, p. 1995 - 2004 (2003)
The ability of chiral anions, for example bis[1,1′-bi-2-naphtholato]borate, to induce asymmetry in the reactions of prochiral cations was investigated. Ion-pairing of a borate anion with an aziridinium ion was demonstrated by NMR spectroscopy. The additio
Hydrogen Bonding Phase-Transfer Catalysis with Potassium Fluoride: Enantioselective Synthesis of β-Fluoroamines
Pupo, Gabriele,Vicini, Anna Chiara,Ascough, David M. H.,Ibba, Francesco,Christensen, Kirsten E.,Thompson, Amber L.,Brown, John M.,Paton, Robert S.,Gouverneur, Véronique
supporting information, p. 2878 - 2883 (2019/02/14)
Potassium fluoride (KF) is an ideal reagent for fluorination because it is safe, easy to handle and low-cost. However, poor solubility in organic solvents coupled with limited strategies to control its reactivity has discouraged its use for asymmetric C-F
Quaternary ammoniums and a cationic sodium complex as supramolecular catalysts in ring-opening of epoxides by amines
Thomas, Coralie,Brut, Sébastien,Bibal, Brigitte
, p. 1646 - 1650 (2014/02/14)
Supramolecular ionic organocatalysts and a metal-based catalyst were investigated in the ring-opening of epoxides by amines, without any artifice to enhance conversion (i.e., solvophobic effect, extended reaction time, heating, excess of amine, high catalyst loading). Different β-amino-alcohols were obtained in satisfying conversion (50-80%) in 24 h, under mild conditions.
Oxidative photofragmentation of α,β-amino alcohols via single electron transfer: Cooperative reactivity of donor and acceptor ion radicals in photogenerated contact radical ion pairs
Ci, Xiaohong,Kellett, Matthew A.,Whitten, David G.
, p. 3893 - 3903 (2007/10/02)
The studies presented in this paper show that α,β-amino alcohols undergo a very clean C-C bond cleavage upon SET (single electron transfer) oxidation by photoexcited electron acceptors in a process which generally culminates in two-electron reduction of the acceptors. For a number of different α,β-amino alcohols, the oxidative fragmentation occurs in a high chemical yield (>90%), yet with low to medium quantum efficiencies (0.0001-0.1) which vary strongly depending on the properties of electron donor (D), acceptor (A), and solvent. The net quantum efficiency reflects the competition between back electron transfer and the chemical redox process. Detailed mechanistic studies were carried out to investigate the visible light induced oxidative fragmentation of α,β-amino alcohols in the presence of electron acceptors including, thioindigo (TI), 9,10-dicyanoanthracene (DCA), 2,6,9,10-tetracyanoanthracene (TCA), and 1,4-dicyanonaphthalene (DCN). Cosensitized (biphenyl) photoredox leads to free ions, A- and D+, and moderately efficient unassisted fragmentation of D+. Quenching of 1A* by electron donor (D) to give a solvent separated radical ion pair (SSRIP) leads to a very inefficient reaction. In contrast, quenching to give a contact radical ion pair (CRIP) gives a relatively efficient reaction. This reaction is sensitive to the stereochemistry of the amino alcohol, suggesting a preferred anticoplanar configuration during the C-C bond cleavage process. The critical matching of reactivity of acceptor and donor ion radicals allows a rapid reaction to occur in the relatively narrow time window between formation and decay of the contact radical ion pair.
