136950-40-8Relevant academic research and scientific papers
Catalytic asymmetric epoxidation of unfunctionalized olefins using chiral (salen)manganese(III) complexes
Irie,Noda,Ito,Matsumoto,Katsuki
, p. 481 - 494 (2007/10/02)
Several kinds of chiral (salen)manganese(III) complexes (2 and 3) having chiral salicylaldehyde and chiral ethylenediamine moieties were prepared and used for catalytic asymmetric epoxidation of unfunctionalized olefins with iodosobenzene as a terminal oxidant. Catalysts 2 and 3 were found to show the characteristic substrate specificity for the enantiofacial selection of olefins, respectively. Furthermore, the addition of donor ligands such as pyridine N-oxide or 2-methylimidazole to the epoxidation reaction system was found to alter the enantioselectivity. As a result, the highest enantioselectivity for nonenzaymatic catalytic epoxidation was achieved for (E)-1-phenylpropene (56% ee, with 2c in the presence of 2-methylimidazole), (E)-stilbene (48% ee, with 3a), and dihydronaphthalene (83% ee, with 3a in the presence of pyridine N-oxide)
Enantioselective epoxidation of unfunctionalized olefins using chiral (salen)manganese(III) complexes
Irie,Noda,Ito,Katsuki
, p. 1055 - 1058 (2007/10/02)
Chiral (salen)manganese(III) complexes (3 and 4) were prepared and used for the enantioselective epoxidation of unfunctionalized olefins. The highest enantioselectivity of 48% ee for the catalytic epoxidation of (E)-stilbene was realized by using 3 as a catalyst though much lower enantioselectivity (7% ee) was obtained for that of (E)-1-phenyl-1-propene. In the epoxidation of (Z)-olefins, enantioselectivities were in the range of 68~72% ee by using 3 as a catalyst and 60% ee by using 4.
