Enzyme catalyzed reverse enantiomeric separation of methyl (±)-3-cyclohexene-1-carboxylate

Article abstract of DOI:10.1016/j.tetasy.2004.05.034

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 the resultant enantiomerically pure (S)-(-)-3- cyclohexene-1-carboxylic acid was transformed into (1S,5S)-(-)-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).