Catalytic Epoxidations with Pyridinebis(oxazoline)-Methyltrioxorhenium Complexes and Nitrogen-Containing Catalyst Systems

The epoxidation of olefins with methyltrioxorhenium (MTO) in the presence of various chiral oxazolines and pyridinebis(oxazoline) ligands as well as achiral N‐ligands has been investigated. By applying 1‐octene as a model system, reaction conditions were optimized, and high yields and good chemoselectivity (>90 %) were achieved. By applying other aromatic and aliphatic olefins, similar chemoselectivities and up to 19 % enantioselectivity were obtained. The epoxidation of 1‐octene using methyltrioxorhenium (MTO) in the presence of pyridinebis(oxazoline) and related ligands is reported. Although excellent chemoselectivity (>90 %) and good yields were obtained, low enantioselectivity was observed.