Enzymatic optical resolution of norbornanecarboxylic esters using pig liver esterase
- 1 January 1991
- journal article
- research article
- Published by Wiley in Recueil des Travaux Chimiques des Pays-Bas
- Vol. 110 (5), 175-184
- https://doi.org/10.1002/recl.19911100508
Abstract
The hydrolysis of a series of norbornane‐type carboxylic esters catalyzed by pig liver esterase (PLE) has been investigated. It was found that an exo‐eer function (syn to the C7 methylene group) is hydrolyzed with high preference. Enantioselective hydrolysis can be accomplished when a vicinal carbonyl‐containing function (eer, formyl, acetyl) is present in a trans position with respect to the exo eer. The regiospecificity of the enzymatic hydrolysis has been used for the separation of exo/endo mixtures of the cycloadducts derived from cyclopentadiene and alkene esters. The regiospecificity and enantioselectivity of the enzymatic hydrolysis of norbornane‐type esters were analyzed in terms of Tamm's substrate model and also by Griengl's method.Keywords
This publication has 88 references indexed in Scilit:
- Synthesis of Chloramphenicol via an Enzymatic Enantioselective HydrolysisSynthesis, 1989
- Enzymatic Reactions in Organic Synthesis 4- Hydrolyses of DiestersSynthetic Communications, 1988
- Enzymes in organic synthesis. 42. Investigation of the effects of the isozymal composition of pig liver esterase on its stereoselectivity in preparative-scale ester hydrolysis of asymmetric synthetic valueJournal of the American Chemical Society, 1988
- Enantioselektive Verseifung der Diacetate von 2‐Nitro‐1,3‐diolen mit Schweineleber‐Esterase und Herstellung enantiomerenreiner Derivate von 2‐Nitro‐allylalkoholen (chirale Verknüpfungsreagenzien)Helvetica Chimica Acta, 1988
- Asymmetric hydrogenation in the presence of bicyclic chiral phosphinesReaction Kinetics and Catalysis Letters, 1981
- A Convenient Method for the Control of Selective Ozonizations of OlefinsSynthesis, 1980
- Thermal racemization of (+)-bicyclo[2.2.1]hept-5-ene-trans-2,3-dicarboxylic acid in the melted and solid statesJournal of the American Chemical Society, 1971
- Resolution, Stereochemial Correlation and Maximum Rotations of the Norbornane- and 5-Norbornene-2-carboxylic Acids. Isotope Dilution as an Aid in the Determination of Optical Purity1Journal of the American Chemical Society, 1959
- The Rearrangement of endo-3,6-Methylene-1,2,3,6-tetrahydro-cis-phthalic AnhydrideJournal of the American Chemical Society, 1951
- Endo-Exo-Rearrangement in the Addition of Acids to DicyclopentadieneJournal of the American Chemical Society, 1946