Aerobic Enantioselective Epoxidation of Unfunctionalized Olefins Catalyzed by Optically Active Salen–Manganese (III) Complexes
- 1 August 1994
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 67 (8) , 2248-2256
- https://doi.org/10.1246/bcsj.67.2248
Abstract
Enantioselective epoxidation of unfunctionalized olefins is achieved by the combined use of molecular oxygen and pivalaldehyde in the presence of a catalytic amount of optically active Mn(III)–salen complexes. N-Alkylimidazoles are effective axial ligands to produce optically active epoxides with high enantioselectivities in the present procedure; that is, 1,2-dihydronaphthalene derivatives and 2,2-dialkyl-2H-chromene derivatives are converted into the corresponding optically active epoxides with 60—92% enantiomeric excess. The key intermediates in the present aerobic epoxidation are also discussed.Keywords
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