Stereoselective reduction of unsaturated 1,4-diketones. A practical route to chiral 1,4-diols

Article abstract of DOI:10.1016/S0040-4039(96)02476-8

A new synthetic route to C₂-symmetric chiral 1,4-diols based on the borane-mediated oxazaborolidine-catalysed reduction of 2-ene-1,4-diones (2), of 2-yne-1,4-diones (3), and/or of Co-complexed diketones 4 is described. Good to excellent enantio- and diastereoselectivities have been obtained in the reduction of diketones 3 and 4, catalysed by oxazaborolidines 6 and 5, respectively.