Asymmetric biotransformation of phenyl-C4 derivatives in rat liver (S-9) and baker's yeast

Abstract When phenylbutyne ( 1 ) was incubated in rat liver S-9, reduction of triple bond and regioselective hydroxylation occurred to give phenylbutane ( 3 ) and (2 S )-4-phenyl-3-butyn-2-ol ( 2 ), respectively. In the reaction of ( 1 ) with baker's yeast, reduction of triple bond occurred to give ( 3 ). In the incubation of 4-phenyl-3-buten-2-one ( 6 ) in rat liver, (2 S )-4-phenyl-2-butanol [(2 S )- 8 ] were afforded from control rat liver, while (2 R )-isomers [(2 R )- 8 ] were isolated from PB treated rat liver. 2,3-Epoxy-1-phenyl-1-butanone ( 10 ) was enantioselectively reduced to give the corresponding (1 R ,2 S ,3 R )- and (1 R ,2 R ,3 S )-epoxy alcohols ( 11 , 12 ) in high optical yields in rat liver and baker's yeast. However, in the same reaction of 2,3-epoxy-4-phenyl-2-butanone ( 13 ), reduction of ketone proceeded enantioselectively in baker's yeast to give (1 S ,2 S ,3 R )- and (1 R ,2 R ,3 R )-epoxyalcohols ( 14 , 15 ) in high optical yields (each 98% ee).