Stereoselective Synthesis of Homochiral Alpha Substituted o-Methoxybenzyl Alcohols via Nucleophilic Additions to Kinetically Resolved Homochiral Tricarbonyl(η6-o-anisaldehyde)chromium(0)

Article abstract of DOI:10.1016/S0957-4166(00)80533-9

Tricarbonyl(η⁶-o-anisaldehyde)chromium(0) has been kinetically resolved via the selective hydrolysis of one of the L-valinol derived imine diasteroisomers in the presence of deactivated alumina.An X-ray crystal structure analysis on the adduct formed between L-valinol and homochiral (+)-tricarbonyl(η⁶-o-anisaldehyde)chromium(0) unambiguously established the presence of the corresponding imine and not oxazolidine and confirmed the absolute configuration of the aldehyde complex.Addition of Grignard reagents to homochiral tricarbonyl(η⁶-o-anisaldehyde)chromium(0) occurs completely stereoselectively to give, following decomplexation, homochiral alpha substituted o-methoxybenzyl alcohols.