Multiple Enantioselection by an Enzyme‐Catalyzed Transacylation Reaction

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Abstract
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.