938076-82-5Relevant academic research and scientific papers
Iridium-catalyzed acid-assisted asymmetric hydrogenation of oximes to hydroxylamines
Mas-Roselló, Josep,Smejkal, Tomas,Cramer, Nicolai
, p. 1098 - 1102 (2020)
Asymmetric hydrogenations are among the most practical methods for the synthesis of chiral building blocks at industrial scale. The selective reduction of an oxime to the corresponding chiral hydroxylamine derivative remains a challenging variant because of undesired cleavage of the weak nitrogen-oxygen bond. We report a robust cyclometalated iridium(III) complex bearing a chiral cyclopentadienyl ligand as an efficient catalyst for this reaction operating under highly acidic conditions. Valuable N-alkoxy amines can be accessed at room temperature with nondetected overreduction of the N-O bond. Catalyst turnover numbers up to 4000 and enantiomeric ratios up to 98:2 are observed. The findings serve as a blueprint for the development of metal-catalyzed enantioselective hydrogenations of challenging substrates.
Enantioselective oxidation of O-methyl-N-hydroxylamines using monoamine oxidase N as catalyst
Eve, Tom S. C.,Wells, Andrew,Turner, Nicholas J.
, p. 1530 - 1531 (2008/02/04)
Enantioselective oxidation of racemic O-methyl-N- hydroxycyclohexylethylamine, using a variant of monoamine oxidase N (MAO-N) from Aspergillus niger, yields unreacted (R)-enantiomer (e.e. = 99%) together with the oxime exclusively in the (E)-configuration. The Royal Society of Chemistry.
