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

Date

2004-07-01

Author

Tanyeli, Cihangir
Turkut, E

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

1
views

0
downloads

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

Collections

Department of Chemistry, Article