28523-15-1Relevant articles and documents
Mild Iridium-Catalysed Isomerization of Epoxides. Computational Insights and Application to the Synthesis of β-Alkyl Amines
Cabré, Albert,Cabezas-Giménez, Juanjo,Sciortino, Giuseppe,Ujaque, Gregori,Verdaguer, Xavier,Lledós, Agustí,Riera, Antoni
supporting information, p. 3624 - 3631 (2019/07/10)
The isomerization of epoxides to aldehydes using the readily available Crabtree's reagent is described. The aldehydes were transformed into synthetically useful amines by a one-pot reductive amination using pyrrolidine as imine-formation catalyst. The reactions worked with low catalyst loadings in very mild conditions. The procedure is operationally simple and tolerates a wide range of functional groups. A DFT study of its mechanism is presented showing that the isomerization takes place via an iridium hydride mechanism with a low energy barrier, in agreement with the mild reaction conditions. (Figure presented.).
An electric field-induced change in the selectivity of a metal oxide-catalyzed epoxide rearrangement
Gorin, Craig F.,Beh, Eugene S.,Kanan, Matthew W.
supporting information; experimental part, p. 186 - 189 (2012/03/07)
The rearrangement of cis-stilbene oxide catalyzed by Al2O 3 was studied in the presence of interfacial electric fields. Thin films of Al2O3 deposited on Si electrodes were used as the opposing walls of a reaction vessel. Application of a voltage across the electrodes engendered electrochemical double layer formation at the Al 2O3-solution interface. The aldehyde to ketone product ratio of the rearrangement was increased by up to a factor of 63 as the magnitude of the double layer charge density was increased. The results support a field-dipole effect on the selectivity of the catalytic reaction.
Diastereoselectivity in the reduction of sterically unbiased 2,2-diarylcyclopentanones
Halterman, Ronald L.,McEvoy, Marjorie A.
, p. 6690 - 6695 (2007/10/02)
Reduction of sterically unbiased 2-phenyl-2-(4-X-phenyl)cyclopentanones 1 (X = NO2, Br, Cl, OCH3, OH, NH2) with either sodium borohydride in methanol or lithium borohydride in tetrahydrofuran at 0°C produced diastereomeric