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

Date

2004-07-01

Author

Tanyeli, Cihangir

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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 (1S,5S)-(-)-5-(hydroxymethyl)-2-cyclohexen-1-ol via iodolactonization, subsequent elimination of iodine with 1,8-diazibicyclo[5.4.0]undec-7-ene (DBU) and reduction with lithium aluminum hydride (LAH).

Subject Keywords

Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Catalysis

URI

https://hdl.handle.net/11511/42528

Journal

TETRAHEDRON-ASYMMETRY

DOI

https://doi.org/10.1016/j.tetasy.2004.05.034

Collections

Department of Chemistry, Article

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Citation Formats

C. Tanyeli, “Enzyme catalyzed reverse enantiomeric separation of methyl (+/-)-3-cyclohexene-1-carboxylate,” TETRAHEDRON-ASYMMETRY, pp. 2057–2060, 2004, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/42528.