The
first example of dynamic kinetic resolution (DKR) of chiral unsaturated
carboxylic acids is described. The application of tandem metal–enzyme
DKR is a powerful tool for the manufacture of high-value chemical
commodities. This new protocol of kinetic resolution based on irreversible
enzymatic esterification of 3-aryl-4-pentenoic acids with ortho esters
was introduced to obtain optically active unsaturated carboxylic acids.
This procedure was combined with metal-catalyzed racemization of the
target substrate, providing the optically pure S enantiomer
of ethyl 3-phenylpent-4-enoate with very high isolated yield (98%).
A substantial influence of organic cosolvent and metal catalyst on
the conversion and enantioselectivity of the enzymatic dynamic kinetic
resolution was noted.
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