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The catalytic, enantioselective cyclopropanation of cinnamyl alcohol has been accomplished with bis(iodomethyl)zinc in the presence of chiral bis(sulfonamides) derived from cyclohexanediamine. An extensive survey of diamine and sulfonamide structure has revealed a marked sensitivity to the spatial relationship of the amine groups, but only a modest dependence on the sulfonamide residue.
The rate and selectivity of catalytic enantioselective cyclopropanation of cinnamyl alcohol utilizing bisiodomethyl zinc and 4a4b is greatly dependent on the order of addition of the reagents. The independent preformation of the ethylzinc cinnamyloxide and bis(iodomethyl)zinc was found to be crucial. The reaction displayed autocatalytic behavior which was shown to be due to the generation of zinc...
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