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Enzyme catalyzed reverse enantiomeric separation of methyl (+/-)-3-cyclohexene-1-carboxylate
Date
2004-07-01
Author
Tanyeli, Cihangir
Turkut, E
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This work is licensed under a
Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License
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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