Catalytic asymmetric epoxidation of unfunctionalized olefins

Epoxidation studies of 2-styrylchromones using jacobsen's catalyst and hydrogen peroxide and iodosylbenzene as oxidants

“…Only a few years after this key publication an asymmetric version of this epoxidation was reported by the groups of Jacobsen [18] and Katsuki [19] using chiral Mn(III)-salen complexes as catalyst. Iodosylbenzene [17][18][19][20][21][22][23] and sodium hypochlorite [24][25][26] are the most frequently used terminal oxidants but other oxygen sources such as hydrogen peroxide [27][28][29][30], dimethyldioxirane (DMD) [31][32][33], Oxone ® [34], tetrabutylammonium monopersulfate [35], tetrabutylammonium periodate [36], mchloroperoxybenzoic acid [37] and even molecular oxygen [38] have been reported. Iodosylbenzene is a polymeric substance, prepared by base-induced hydrolysis of the commercially available iodobenzene diacetate, and the role of the catalyst in homogeneous catalysis is to solubilise it in its monomeric form.…”

Epoxidation Studies of 2‐Styrylchromones Using Jacobsen′s Catalyst and Hydrogen Peroxide and Iodosylbenzene as Oxidants.

“…Only a few years after this key publication an asymmetric version of this epoxidation was reported by the groups of Jacobsen [18] and Katsuki [19] using chiral Mn(III)-salen complexes as catalyst. Iodosylbenzene [17][18][19][20][21][22][23] and sodium hypochlorite [24][25][26] are the most frequently used terminal oxidants but other oxygen sources such as hydrogen peroxide [27][28][29][30], dimethyldioxirane (DMD) [31][32][33], Oxone ® [34], tetrabutylammonium monopersulfate [35], tetrabutylammonium periodate [36], mchloroperoxybenzoic acid [37] and even molecular oxygen [38] have been reported. Iodosylbenzene is a polymeric substance, prepared by base-induced hydrolysis of the commercially available iodobenzene diacetate, and the role of the catalyst in homogeneous catalysis is to solubilise it in its monomeric form.…”

Manganese and cobalt 3-oxobutylideneaminato complexes: Design and application for enantioselective reactions

“…For example, the enantioselective epoxidation of various alkenes are so far performed using other oxidants, such as iodosylbenzene [5][6][7], sodium hypochlorite [8], and peracid [9], to afford the corresponding epoxides with high-toexcellent enantioselectivities in the presence of salen-Mn(III) complex catalysts. By the combined use of molecular oxygen and secondary alcohols, the terminal alkenes were converted to the corresponding hydrated products in the presence of cobalt(II) complexes having 1,3-diketone-type ligands.…”