Regio- and Stereo-selective Bioreduction of Diketo-n-butylphosphonate by Baker's Yeast

A regio- and stereo-selective reduction of diketo-n-butylphosphonates by baker's yeast was reported. The chemical yield and ee value of these reactions are highly dependent on the structure of substrates. The resulting optical active hydroxyalkanephosphonates can be used as chirons for the synthesis of polyfunctional organophosphorus compounds. As useful building block, a series of α, β-unsaturated ketones bearing chiral hydroxy group in addition to trifluoromethyl moiety was prepared via the Homer-Wadsworth-Emmons (HWE) reaction of the biotransformation products.