MULTIPLE ENANTIOSELECTION BY AN ENZYME-CATALYZED TRANSACYLATION REACTION

Multiply enantioselective enzyme-catalyzed transacylation reactions are described. Two instances of triply enantioselective enzyme-catalyzed transacylations are 1) the reaction of rac-1-indanol with rac-1,1'-bi-2-naphthyl-2,2'-dibutyrate to afford (S)-1-indanol, (R)-1-indanylacetate, (S)-1,1'-bi-2-naphthyl-2,2'-diol, and (R)-1,1'-bi-2-naphthyl-2,2'-dibutyrate and 2) the reaction of rac-1-indanol with rac-2,2'-bis(butyroxymethyl)biphenyl to afford (S)-1-indanol, (R)-1-indanylbutyrate, (S)-2,2'-biphenyldimethanol, and (R)-2,2'-bis(butyroxy-methyl)biphenyl. Doubly enantioselective enzyme-catalyzed transacylations are described according to two instances: 1) the reaction of rac-1-indanol with rac-1,1'-bi-2-naphthyl-2-ol-2'-butyrate afforded (S)-1-indanol, (R)-1-indanylacetate, (S)-1,1'-bi-2-naphthyl-2,2'-diol, and (R)-1,1'-bi-2-naphthyl-2-ol-2'-butyrate, and 2) the reaction of rac-1-indanol with 1,3,5-O-methylidne-2,4,6-tri-O-butyrate-myo-inositol to afford (S)-l-indanol, (R)-l-indanylbutyrate, and 1,3,5-O-methylidne-2,6-di-O-butyrate-myo-inositol. Multiply enantioselective enzyme-catalyzed reactions have a merit of the enhancement of enantiomeric excess over singly enantioselective ones.