Journal of Organic Chemistry p. 5253 - 5254 (1991)
Update date:2022-08-10
Topics:
Halterman, Ronald L.
Jan, Shyi-Tai
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.
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