Abstract
Malonic ester synthesis combined with lipase-catalyzed enantioselective partial hydrolysis was used to prepare enantiomers of ethyl 4,4,4-trifluoro-3-(indole-3-)butyrate, a novel plant growth regulator. Among six commercially available enzymes, lipase AK (a lipase from Pseudomonas sp.) showed high enantioselectivity and moderate reactivity. The hydrolysis of racemic diethyl 2,2,2-trifluoro-1-(indole-3-)ethylmalonate (DTFIE) with lipase AK gave, following usual treatment of the products, S-(+)-4,4,4-trifluoro-3-(indole-3-)butyric acid (TFIBA) ethyl ester having 95% e.e. and R-(−)-TFIBA ethyl ester having >99% e.e. The optimized conditions for lipase AK hydrolysis were 0.1 M phosphate buffer (pH 6.0) containing 10% hexane at 45°C.
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