Catalytic Asymmetric Epoxidation of Unfunctionalized Alkenes Using the First D4-Symmetric Metallotetraphenylporphyrin

Article abstract of DOI:10.1021/jo00018a008

The condensation of the resolved C₂-symmetric benzaldehyde, 1,2,3,4,5,6,7,8-octahydro-1:4,5:8-dimethanoanthracene-9-carboxaldehyde, with pyrrole produced a new chiral tetraphenylporphyrin exhibiting D₄ symmetry.A manganese chloride complex of this porphyrin was used as a catalyst (0.5 mol percent) for the asymmetric epoxidation of aromatic-substituted alkenes in the presence of excess sodium hypochlorite, providing for terminal or Z alkene yields above 90 percent and enantioselectivities ranging from 41 to 76 percent ee.