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-naphthy]-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)-1 -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.