31139-02-3Relevant academic research and scientific papers
Scale-up of a recombinant pig liver esterase-catalyzed desymmetrization of dimethyl cyclohex-4-ene-cis-1,2-dicarboxylate
Suess, Philipp,Illner, Sabine,Von Langermann, Jan,Borchert, Sonja,Bornscheuer, Uwe T.,Wardenga, Rainer,Kragl, Udo
, p. 897 - 903 (2014)
A recombinant isoenzyme of pig liver esterase was used for the highly enantioselective desymmetrization of dimethyl cyclohex-4-ene-cis-1,2- dicarboxylate. The selected recombinant esterase showed a significant advantage in enantioselectivity over the comm
Bifunctional organocatalyst for methanolytic desymmetrization of cyclic anhydrides: Increasing enantioselectivity by catalyst dilution
Rho, Ho Sik,Oh, Sang Ho,Lee, Ji Woong,Lee, Jin Yong,Chin, Jik,Song, Choong Eui
, p. 1208 - 1210 (2008)
Highly enantioselective methanolysis of meso-cyclic anhydride was achieved with bifunctional organocatalyst containing a quinine-thiourea moiety; unusual concentration, temperature and solvent effects on the enantioselectivity can be explained in terms of
Chemoenzymatic Sequential Multistep One-Pot Reaction for the Synthesis of (1S,2R)-1-(Methoxycarbonyl)cyclohex-4-ene-2-carboxylic Acid with Recombinant Pig Liver Esterase
Süss, Philipp,Borchert, Sonja,Wardenga, Rainer,Hinze, Janine,Illner, Sabine,Von Langermann, Jan,Kragl, Udo,Bornscheuer, Uwe T.
, p. 2034 - 2038 (2015)
In this work, the development of a chemoenzymatic process for the production of (1S,2R)-1-(methoxycarbonyl)cyclohex-4-ene-2-carboxylic acid by ECS-PLE06 (recombinant pig liver esterase) is presented. Herein an optimized esterification protocol, starting f
Scoping the Enantioselective Desymmetrization of a Poorly Water-Soluble Diester by Recombinant Pig Liver Esterase
Meissner, Murray P.,Süss, Philipp,Brundiek, Henrike,Woodley, John M.,Von Langermann, Jan
, p. 1518 - 1523 (2018)
Previously, the biocatalytic desymmetrization of dimethyl cyclohex-4-ene-cis-1,2-dicarboxylate to (1S,2R)-1-(methoxycarbonyl)cyclohex-4-ene-2-carboxylic acid, an important intermediate toward the synthesis of biologically active molecules, had been well-c
Simple and highly enantioselective nonenzymatic ring opening of cyclic prochiral anhydrides
Bolm, Carsten,Gerlach, Arne,Dinter, Christian L.
, p. 195 - 196 (1999)
A convenient highly enantioselective methanolysis of cyclic meso- anhydrides only requires one equivalent cinchona alkaloid and low temperature. Both enantiomers can be easily obtained with up to 98% ee by using either quinine or quinidine.
Enzymatic desymmetrization of dimethyl cylcohex-4-ene-cis-1,2-dicarboxylate to (1S,2R)-2-(methoxycarbonyl)cyclohex-4-ene-1-carboxylic acid
Goswami, Animesh,Kissick, Thomas P.
, p. 483 - 488 (2009)
An efficient process for the synthesis of the monoester, (1S,2R)- 2-(methoxycarbonyl)cyclohex-4-ene-1-carboxylic acid by Candida antarctica lipase (Novozym 435)-catalyzed desymmetrization of the corresponding diester, dimethyl-cyclohex-4-ene-cis-1,2-dicar
Asymmetric hydrolysis of a meso-diester using pig liver esterase immobilised in hollow fibre ultrafiltration membrane
Sousa, Helena A.,Crespo, Joao G.,Afonso, Carlos A.M.
, p. 929 - 934 (2000)
Pig liver esterase (PLE) was physically immobilised in a polysulphone ultrafiltration hollow fibre membrane reactor and used for the repetitive batch two-phase hydrolysis and separation, on a multigram scale, of the meso-diester dimethyl cis-cycloxex-4-en
The potential of membrane reactors in the asymmetric opening of meso-anhydrides
W?ltinger, Jens,Krimmer, Hans-Peter,Drauz, Karlheinz
, p. 8531 - 8533 (2002)
A polymer attached cinchona-alkaloid was investigated in the asymmetric opening of meso-anhydrides. Variation of reaction parameters reduced the reaction time to 1 hour, which is very important for a continuous reaction. It turned out that due to product
Ionic Liquid Gels: Supramolecular Reaction Media for the Alcoholysis of Anhydrides
Rizzo, Carla,Mandoli, Alessandro,Marullo, Salvatore,D'Anna, Francesca
, p. 6356 - 6365 (2019)
The search of new enantioselective catalysts, able to promote synthetically useful organic reactions with high levels of asymmetric induction, should be associated with the attention to the suitable reaction medium able to achieve the best efficiency in c
The New Catalyst System: Chloramphenicol Base and Organic Acid Co-catalyzed Enantioselective Alcoholysis of meso-Anhydride
Chen, Lu,Liu, Da-Ming,Ma, Chao,Sun, Chen,Wang, Zhong-Hua,Xiong, Fei,Zhang, Yan-Jun,Zhu, Yi-Ren
, p. 9 - 13 (2022/03/27)
In this study, the synergistic catalytic strategy was developed, which chloramphenicol base and organic acid were used in the same system, the optimal enantioselectivity value and yield (96% yield; 65% ee) was achieved using the binary co-catalyst in the asymmetric alcoholysis reaction of mesoanhydride. Moreover, a hypothetical intermediate between the substrate and the binary co-catalyst which is responsible for stereochemistry control in this catalytic reaction was proposed. In addition, the results of molecular mechanics calculations also have shed light on the corresponding catalytic mechanism.
