Chemoenzymatic synthesis of chiral epoxides. Preparation of 4-phenyl-2,3- epoxybutane and 1-phenyl-1,2-epoxypropane

Article abstract of DOI:10.1016/0957-4166(94)80167-3

All the stereoisomers of 4-phenyl-2,3-epoxybutane and 1-phenyl-1,2- epoxypropane (β-methylstyrene oxide) have been prepared in three steps from 4-phenyl-2-butanone and 1-phenyl-2-propanone or 1-phenyl-1-propanone respectively. The key step is the microbiological reduction of the corresponding haloketones. These results confirm those previously described and demonstrate that the chemoenzymatic synthesis of homochiral 2,3-epoxides is a general method that can be used whatever the starting ketone.