Organic carbonates as solvents in macrocyclic Mn(III) salen catalyzed asymmetric epoxidation of non-functionalized olefins

0392334 - ÚOCHB 2014 RIV NL eng J - Journal Article
Maity, N. Ch. - Rao, G. V. S. - Prathap, Kaniraj Jeya - Abdi, S. H. R. - Kureshy, R. I. - Khan, N. H. - Bajaj, H. C.
Organic carbonates as solvents in macrocyclic Mn(III) salen catalyzed asymmetric epoxidation of non-functionalized olefins.
Journal of Molecular Catalysis A-Chemical. Roč. 366, January (2013), s. 380-389. ISSN 1381-1169
Institutional support: RVO:61388963
Keywords : asymmetric epoxidation * organic carbonate * macrocyclic Mn(III) salen complex
Subject RIV: CF - Physical ; Theoretical Chemistry
Impact factor: 3.679, year: 2013

Organic carbonates, e.g., dimethyl carbonate and propylene carbonate were used as reaction media in enantioselective epoxidation of non-functionalized alkenes by using a series of chiral macrocyclic Mn(III) salen complexes (5 mol%) as catalyst with pyridine N-oxide as an axial base. This protocol worked effectively with urea hydrogen peroxide, as well as sodium hypochlorite as oxidants to give respective epoxides in high yields and ee (up to >91% in selected cases). Furthermore kinetic studies of the catalytic epoxidation reaction in dimethyl carbonate:methanol (optimized solvent mixture) with urea hydrogen peroxide as an oxidant showed first order dependence on catalyst and oxidant whereas it is zero order for the substrate, styrene.
Permanent Link: http://hdl.handle.net/11104/0221222