186296-16-2Relevant academic research and scientific papers
Rhodium-catalyzed enantioselective hydrogenation of oxime acetates
Huang, Kexuan,Li, Shengkun,Chang, Mingxin,Zhang, Xumu
, p. 484 - 487 (2013)
Rh-catalyzed enantioselective hydrogenation of oxime acetates was first reported, which afforded a new approach for chiral amine synthesis.
Biocatalytic, Intermolecular C?H Bond Functionalization for the Synthesis of Enantioenriched Amides
Arnold, Frances H.,Athavale, Soumitra V.,Gao, Shilong,Hirschi, Jennifer S.,Liu, Zhen,Mallojjala, Sharath Chandra
supporting information, p. 24864 - 24869 (2021/10/15)
Directed evolution of heme proteins has opened access to new-to-nature enzymatic activity that can be harnessed to tackle synthetic challenges. Among these, reactions resulting from active site iron-nitrenoid intermediates present a powerful strategy to forge C?N bonds with high site- and stereoselectivity. Here we report a biocatalytic, intermolecular benzylic C?H amidation reaction operating at mild and scalable conditions. With hydroxamate esters as nitrene precursors, feedstock aromatic compounds can be converted to chiral amides with excellent enantioselectivity (up to >99 % ee) and high yields (up to 87 %). Kinetic and computational analysis of the enzymatic reaction reveals rate-determining nitrenoid formation followed by stepwise hydrogen atom transfer-mediated C?H functionalization.
C-H Amination via Electrophotocatalytic Ritter-Type Reaction
Lambert, Tristan H.,Shen, Tao
supporting information, p. 8597 - 8602 (2021/06/28)
A method for C-H bond amination via an electrophotocatalytic Ritter-Type reaction is described. The reaction is catalyzed by a trisaminocyclopropenium (TAC) ion in an electrochemical cell under irradiation. These conditions convert benzylic C-H bonds to acetamides without the use of a stoichiometric chemical oxidant. A range of functionality is shown to be compatible with this transformation, and several complex substrates are demonstrated.
