Abstract
We describe the differences of hydrolase-type enzymes pig liver esterase (PLE), horse liver esterase (HLE), and porcine pancreatic lipase (PPL) on the hydrolysis of methyl (±)-3-cyclohexene-1-carboxylate to afford both enantiomers with 89% to >99% ee. The resultant enantiomerically pure ( S)-(−)-3-cyclohexene-1-carboxylic acid was transformed into (1 S,5 S)-(−)-5-(hydroxymethyl)-2-cyclohexen-1-ol via iodolactonization, subsequent elimination of iodine with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and reduction with lithium aluminum hydride (LAH).
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