Transition metal mediated asymmetric synthesis VII. 6-Methoxycyclohexadienyliron complexes: access to synthetic equivalents of cyclohexadiene dications

Article abstract of DOI:10.1016/S0022-328X(00)99399-9

The dimethyl ether of cyclohexa-1,3-diene-5,6-diol, available via microbial oxidation of benzene, was converted into the tricarbonyl-(η⁵-6-methoxycyclohexadienyl)-iron(1+) complex (1) by complexation and demethoxylation with TFA.Alkylation and demethoxylation produced a 6-methyl intermediate; the corresponding 6-butyl salt was also obtained.The stereochemistry of complex 1 was determined by conversion into the endo,exo-dimethoxy substituted complex 8 by reaction with sodium metoxide.