Transition metal mediated asymmetric synthesis. X. Homochiral ?-complexes with planar chirality: synthetic equivalents of chiral cyclohexadiene dications

Article abstract of DOI:10.1016/0022-328X(89)87278-X

Homochiral 6-methoxy-substituted dienyltricarbonyliron complexes have been obtained from 1-methylcyclohexa-1,3-diene-5,6-diol (available via microbial oxidation of toluene) by complexation and removal of an allylic substituent with acids or with triphenylcarbenium tetrfluoroborate.A variety of optically active tricarbonyliron complexes have been produced from these compounds.The optical purity of the product and the stereochemistry of the complexation reaction have been determined.The high efficiency of chirality transfer during complexation of 5,6-dimethoxy-substituted dienes makes this method suitable as a general route to resolved organoiron complexes.