143169-28-2Relevant academic research and scientific papers
Enantioconvergent transformation of racemic cis-β-alkyl substituted styrene oxides to (R,R) threo diols by microsomal epoxide hydrolase catalysed hydrolysis
Bellucci, Giuseppe,Chiappe, Cinzia,Cordoni, Antonio
, p. 197 - 202 (2007/10/03)
Both enantiomers of cis-β-ethyl, β-n-propyl, β-n-butyl, and β-n-hexyl substituted styrene oxides undergo microsomal epoxide hydrolase catalysed hydration at the (S) carbon to give the corresponding (R, R) threo diols in a > 90% e.e. A complete kinetic resolution of the racemic epoxide is also obtained with the β-ethyl substituted substrate, but not with its higher homologues.
Enzymatic Synthesis of Chiral 1-Phenyl-1,2- and 1,3-diols via Chiral Epoxy Alcohols
Takeshita, Mitsuhiro,Miura, Masatomo,Unuma, Yukiko
, p. 2901 - 2906 (2007/10/02)
Chiral epoxy alcohols have been prepared by asymmetric reduction of 1-phenyl-2,3-epoxybutan-1-one with baker's yeast, or by enantioselective esterification of racemic 1-phenyl-2,3-epoxybutan-1-one with lipase PS.The epoxyalcohols obtained were reduced with lithium aluminium hydride to afford chiral 1-phenylbutane-1,2- and 1,3-diols.The absolute configurations of the epoxy alcohols and diols were determined by use of modified Mosher's method or by comparison with the diols, which were prepared from benzoylacetone via chiral enols by use of baker's yeast and lipase PS.
