Fluoromethylated imines, aldolase antibody reaction

REACTION OF FLUOROMETHYLATED IMINES USING ANTIBODY ALDOLASE 38C2-IONIC LIOUID SYSTEM... 

On the basis of encouraging work in the development of L-proline-DMSO and L-proline-ionic liquid systems for practical asymmetric aldol reactions, an aldolase antibody 38C2 was evaluated in the ionic liquid [BMIM]PF6 as a reusable aldolase-ionic liquid catalytic system for the aldol synthesis of oc-chloro- 3-hydroxy compounds (288). The biocatalytic process was followed by chemical catalysis using Et3N in the ionic liquid [BMIM]TfO at room temperature, which transformed the oc-chloro-(3-hydroxy compounds to the optically active (70% ee) oc, (3-epoxy carbonyl compounds. The aldolase antibody 38C2-ionic liquid system was also shown to be reusable for Michael additions and the reaction of fluoromethylated imines. 

We carried out a reaction of fluoromethylated imines with hydroxyacetone in the antibody aldolase 38C2-ionic liquid system. In this system the reaction did not proceed in the absence of antibody aldolase 38C2. In the presence of antibody aldolase 38C2, the reaction smoothly proceeded, giving a fluoromethylated carbinol. 

Proposed reaction mechanism is shown in Scheme 10.8. Note the reaction paths of the fluoromethylated imines with hydroxyacetone in antibody aldolase 38C2-ionic liquid in the scheme. At first an intermediate reaction and H2O are produced... 

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