Relevant bibliographies by topics / Enantioselective hydrolyses

Academic literature on the topic 'Enantioselective hydrolyses'

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Published: 10 December 2022
Last updated: 29 January 2023

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Journal articles on the topic "Enantioselective hydrolyses"

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Glänzer, B. I., K. Faber, and H. Griengl. "Enantioselective hydrolyses by baker's yeast - II." Tetrahedron 43, no. 4 (1987): 771–78. http://dx.doi.org/10.1016/s0040-4020(01)90011-0.

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Tafi, Andrea, Andreas van Almsick, Federico Corelli, Maria Crusco, Kurt E. Laumen, Manfred P. Schneider, and Maurizio Botta. "Computer Simulations of Enantioselective Ester Hydrolyses Catalyzed byPseudomonas cepaciaLipase†." Journal of Organic Chemistry 65, no. 12 (June 2000): 3659–65. http://dx.doi.org/10.1021/jo9919198.

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Kasai, Masaji, Herman Ziffer, and J. V. Silverton. "Enantioselective ester hydrolyses using Rhizopusnigricans: stereoselective synthesis and absolute stereochemistry of (−)-cis- and (−)-trans-1-hydroxy-4-methyl-1,2,3,4-tetrahydronaphthalene." Canadian Journal of Chemistry 63, no. 6 (June 1, 1985): 1287–91. http://dx.doi.org/10.1139/v85-219.

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Enantioselective hydrolysis of racemic acetates of cis- and trans-1-hydroxy-4-methyl-1,2,3,4-tetrahydronaphthalene using Rhizopusnigricans yields chiral alcohols. The absolutestereochemistry of these compounds, and that of a key intermediate in their stereoselective synthesis, r-1-hydroxy-2,t-bromo-4,c-methyl-1,2,3,4-tetrahydronaphthalene, were determined by chemical transformations to 1-oxo-4-methyl-1,2,3,4-tetrahydronaphthalene of known absolute stereochemistry. The relativestereochemistry of the acetate of the key intermediate was established by X-ray crystallography.
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Xie, Zhuo-Feng, Izumi Nakamura, Hiroshi Suemune, and Kiyoshi Sakai. "An insight into the enantioselective hydrolyses of cyclic acetates catalysed by Pseudomonas fluorescens lipase." Journal of the Chemical Society, Chemical Communications, no. 14 (1988): 966. http://dx.doi.org/10.1039/c39880000966.

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Utsumi, Ryoichi, Shunsuke Izumi, and Toshifumi Hirata. "Enantioselective hydrolyses of α-methylated cyclohexyl acetates by the cultured cells of Marchantia polymorpha." Journal of Molecular Catalysis B: Enzymatic 11, no. 4-6 (January 2001): 439–43. http://dx.doi.org/10.1016/s1381-1177(00)00158-2.

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Deardorff, Donald R., Roberto B. Amador, James W. Morton, Henry Y. Kim, Cullen M. Taniguchi, Arnel A. Balbuena, Sam A. Warren, Vadim Fanous, and S. W. Tina Choe. "Chiral induction in cyclopentyl-derived 1,3-meso-diesters: enantioselective hydrolyses with electric eel acetylcholinesterase." Tetrahedron: Asymmetry 10, no. 11 (June 1999): 2139–52. http://dx.doi.org/10.1016/s0957-4166(99)00236-0.

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Csuk, René, and Petra Dörr. "Biocatalytical transformations. IV. Enantioselective enzymatic hydrolyses of building blocks for the synthesis of carbocyclic nucleosides." Tetrahedron: Asymmetry 5, no. 2 (January 1994): 269–76. http://dx.doi.org/10.1016/s0957-4166(00)86183-2.

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Fantin, Giancarlo, Marco Fogagnolo, Alessandra Guerrini, Alessandro Medici, Paola Pedrini, and Silvia Fontana. "Enantioselective hydrolyses with Yarrowia lipolytica: a versatile strain for esters, enol esters, epoxides, and lactones." Tetrahedron: Asymmetry 12, no. 19 (October 2001): 2709–13. http://dx.doi.org/10.1016/s0957-4166(01)00463-3.

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Gu, Rui-Lin, Ik-Soo Lee, and Charles J. Sih. "Chemo-enzymatic asymmetric synthesis of amino acids. Enantioselective hydrolyses of 2-phenyl-oxazolin-5-ones." Tetrahedron Letters 33, no. 15 (April 1992): 1953–56. http://dx.doi.org/10.1016/0040-4039(92)88111-h.

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Martinez-Rodríguez, Sergio, Rafael Contreras-Montoya, Jesús M. Torres, Luis Álvarez de Cienfuegos, and Jose Antonio Gavira. "A New L-Proline Amide Hydrolase with Potential Application within the Amidase Process." Crystals 12, no. 1 (December 23, 2021): 18. http://dx.doi.org/10.3390/cryst12010018.

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L-proline amide hydrolase (PAH, EC 3.5.1.101) is a barely described enzyme belonging to the peptidase S33 family, and is highly similar to prolyl aminopeptidases (PAP, EC. 3.4.11.5). Besides being an S-stereoselective character towards piperidine-based carboxamides, this enzyme also hydrolyses different L-amino acid amides, turning it into a potential biocatalyst within the Amidase Process. In this work, we report the characterization of L-proline amide hydrolase from Pseudomonas syringae (PsyPAH) together with the first X-ray structure for this class of L-amino acid amidases. Recombinant PsyPAH showed optimal conditions at pH 7.0 and 35 °C, with an apparent thermal melting temperature of 46 °C. The enzyme behaved as a monomer at the optimal pH. The L-enantioselective hydrolytic activity towards different canonical and non-canonical amino-acid amides was confirmed. Structural analysis suggests key residues in the enzymatic activity.
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Dissertations / Theses on the topic "Enantioselective hydrolyses"

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Kerry, Simon. "Investigation of enantioselective hydrolyses with fungal hydrolase systems." Thesis, Loughborough University, 1989. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.329713.

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Beard, Timothy Mark. "Enzyme catalysed hydrolysis of nitriles and amides." Thesis, University of Huddersfield, 1996. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.363237.

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Described in this thesis is the isolation of two microorganisms containing a nitrile hydratase and amidase to effect the enantioselective hydrolysis of a-substituted nitriles to their corresponding amides and acids. Isolate NP3854 was identified as an atypical Rhodococcus sp. The nitrile hydratase proved to be non-selective for all the substrates tested. However, carboxylic acids with excellent enantiomeric excess were obtained from a large number of amides. X R~CN H nitr-il-e--h-y-d-r.a~tase ~X amidas.e RH CONH2 X R~"""CO H H 2 Optically active acids with an enantiomeric excess of, generally, >98 %, were obtained when X = NH2, Me and Cl, but proved to be racemic for OH and Br. R could be a variety of aromatic, cyclic and acyclic alkyl residues without adversely affecting the enantioselectivity. The pH-activity profile was determined for the amidase of NP3854 using propionamide as the substrate. From this data, coupled with inhibition studies, it may ,.tentatively be suggested that the amidase has a histidine residue in the active site, which may act as a general base for a serine amino acid. The pH-activity profile was determined for 2-amino-2-phenylacetamide 2b, and this suggested that the unprotonated form of the amine acted as the substrate. Within a pH range of 3 - 9 the enantiomeric excess remains high (>98 %) and experimentally invariant. The amidase was found to have a temperature optimum of 60°C and could tolerate 20 % THF with a loss of only 15 % activity. Attempts made to hydrolyse 4,5,6-amino nitriles and amides to the corresponding amino acids and isolate any reaction intermediates failed. This was presumed to be due to the large fraction of the unprotonated amine due to the higher pKa (- 9 - 10).
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Hussain, Sajad. "Enantioselective hydrolysis of phenylglycineamide to phenylglycine by Rhodococcus NP3854." Thesis, Keele University, 2003. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.288510.

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Chauveau, Viriot Christine. "Synthèse de dérivés 3-aryloxypropioniques en mélange racémique et sous forme enantiomeriquement pure : utilisation dans la préparation de quelques hétérocycles." Nancy 1, 1991. http://www.theses.fr/1991NAN10132.

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Les acides et esters 2-alkyl 3-aryloxypropioniques sont préparés à partir d'éthers chloromethyliques aromatiques et d'alkylmalonates. Une résolution par hydrolyse enzymatique permet d'obtenir chacun des énantiomères avec une bonne sélectivité. Les acides donnent accès aux 3-alkyl 4-chromanones correspondantes. Parallèlement différents acides et esters 3-aryloxy 2-hydroxy-propioniques sont obtenus avec de bons rendements au moyen de deux méthodes complémentaires. L'une implique ethers chloromethyliques aromatiques et acetoxymalonate, l'autre implique la préparation de 3-aryloxy 2-hydroxypropionitrile et son hydrolyse. Quelques propriétés chimiques de ces dérivés sont mis en évidence
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Nelson, Keegan Gregory. "Enantioselective hydrolysis of 1-arylpropargylic esters by enzymatic kinetic resolution and dynamic kinetic resolution of 1-arylallylic esters." Thesis, University of Missouri - Kansas City, 2013. http://pqdtopen.proquest.com/#viewpdf?dispub=1538847.

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Chiral 1-arylprop-2-en-1-ols and 1-arylprop-2-yn-1-ols are useful building blocks for modern pharmaceuticals. Previous work has found that enzyme catalysis is a potential new enantioselective synthetic route to the former. We found that Candida antarctica lipase is also an effective catalyst for kinetic resolution of various substituted 1 arylpropargylic acetates and haloacetates, affording the respective (R) -1 arylproargylic alcohols with high enantioselectivity (99-100% ee). By varying the substituents on both sides of the ester bond, we discovered that the deacylation of lipase is likely the rate-determining step for our catalytic system. A greater challenge is designing a dynamic kinetic resolution (DKR) system for such substrates, which combines a resolving catalyst (lipase) with a racemizing catalyst, and can potentially lead to quantitative conversion of a racemic substrate into an enantiopure product. We studied the efficacy of various transition-metal complexes for substrate racemization and will report our results for In and Cu compounds.

While kinetic resolution has been performed on the 1-arylallylic acetates with excellent yield and enantioselectivity and the DKR regime has been designed, the resulting site-isolation system has required further testing and fine tuning. We have herein investigated the utilization of macroscale site-isolation as well as various factors including solvent, and acyl donor effects in order to optimize conditions of the system.

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Miao, Lei. "Synthesis of Amphibian Alkaloids and Development of Acetaminophen Analogues." ScholarWorks@UNO, 2009. http://scholarworks.uno.edu/td/985.

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The focus of these studies has been toward the development of new synthetic methods and procedures for the synthesis of novel compounds with unique biological properties. This research has led to the development of two new synthetic strategies for the construction of two novel amphibian alkaloids. In addition, the efforts have led to the large-scale process for the preparation of a novel analgesic compound. The regioselective ring opening of lactones (δ-valerolactone and γ-butyrolactone) with aryllithium reagents is reported for the construction of a series of δ-hydroxyarylketones and γ-hydroxyarylketones. Both the R and S enantiomers of the amphibian alkaloid noranabasamine were prepared in >30% overall yield with 80% ee and 86% ee, respectively. An enantioselective iridium-catalyzed N-heterocyclization reaction with either (R)- or (S)-1-phenylethylamine and 1-(5-methoxypyridin-3-yl)-1, 5-pentanediol was employed to generate the 2-(pyridin-3-yl)-piperidine ring system in 69-72% yield. A cis-2, 5-disubstitued pyrrolidine building block derived from (-)-Cocaine•HCl was prepared. We utilized this compound as a chiral building block for the formal synthesis of (+)-gephyrotoxin. Using this pyrrolidine building block, Kishi's intermediate was obtained enantiospecifically in 15 steps and 9.4% overall yield. A large-scale process for the preparation of the analgesic compounds SCP-123 and its sodium salt, SCP-123ss•monohydrate has been developed. The process for the preparation of SCP-123 required three synthetic steps with no chromatography, while the process for the preparation of SCP-123ss required four synthetic steps and no chromatography. The overall yields for both SCP-123 and SCP-123ss were 47% and 46%, respectively, and both compounds were obtained in exceptionally high purity (>99%).
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Books on the topic "Enantioselective hydrolyses"

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Kerry, Simon. Investigation of enantioselective hydrolyses with fungal hydrolase systems. 1989.

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Book chapters on the topic "Enantioselective hydrolyses"

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Smeets, J. W. H., and A. P. G. Kieboom. "Enzymatic enantioselective ester hydrolysis by carboxylesterase NP." In Microbial Reagents in Organic Synthesis, 273–88. Dordrecht: Springer Netherlands, 1992. http://dx.doi.org/10.1007/978-94-011-2444-7_22.

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Bodanszky, Miklos, and Agnes Bodanszky. "Synthesis and Enantioselective Enzymic Hydrolysis of Tetraalanine [1]." In The Practice of Peptide Synthesis, 191–92. Berlin, Heidelberg: Springer Berlin Heidelberg, 1994. http://dx.doi.org/10.1007/978-3-642-85055-4_30.

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Riefling, B. F., W. K. Brümmer, and H. J. Gais. "Enantioselective Ple-Catalyzed Hydrolysis of Meso-Dimethyl Tetrahydrophthalate on a 100 Mole Scale — Protection of the Enzyme by Addition of Bovine Serum Albumin." In Enzymes as Catalysts in Organic Synthesis, 347. Dordrecht: Springer Netherlands, 1986. http://dx.doi.org/10.1007/978-94-009-4686-6_22.

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Taber, Douglass. "Enantioselective Assembly of Oxygenated Stereogenic Centers." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0032.

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Reaction with an enantiomerically-pure epoxide is an efficient way to construct a molecule incorporating an enantiomerically-pure oxygenated stereogenic center. The Jacobsen hydrolytic resolution has made such enantiomerically-pure epoxides readily available from the corresponding racemates. Christopher Jones and Marcus Weck of the Georgia Institute of Technology have now (J. Am. Chem. Soc. 2007, 129, 1105) developed an oligomeric salen complex that effects the enantioselective hydrolysis at remarkably low catalyst loading. Any such approach depends on monitoring the progress of the hydrolysis, usually by chiral GC or HPLC. In a complementary approach, we (J. Org. Chem. 2007, 72, 431) have found that on exposure to NBS and the inexpensive mandelic acid 2, a terminal alkene such as 1 was converted into the two bromomandelates 3 and 4. These were readily separated by column chromatography. Individually, 3 and 4 can each be carried on the same enantiomer of the epoxide 5. As 3 and 4 are directly enantiomerically pure, epoxide 5 of high ee can be prepared reliably without intermediate monitoring by chiral GC or HPLC. Another way to incorporate an enantiomerically-pure oxygenated stereogenic center into a molecule is the enantioface-selective addition of hydride to a ketone such as 6. Alain Burgos and his team at PPG-SIPSY in France have described (Tetrahedron Lett. 2007, 48, 2123) a NaBH4 -based protocol for taking the Itsuno-Corey reduction to industrial scale. In the past, aldehydes have been efficiently α-oxygenated using two-electron chemistry. Mukund P. Sibi of North Dakota State University has recently (J. Am. Chem. Soc. 2007, 129, 4124) described a novel one-electron alternative. The organocatalyst 10 formed an imine with the aldehyde. One-electron oxidation led to an α-radical, which was trapped by the stable free radical TEMPO to give, after hydrolysis, the α-oxygenated aldehyde 11. High ee oxygenated secondary centers can also be prepared by homologation of aldehydes. Optimization of the enantioselective addition of the inexpensive acetylene surrogate 13 was recently reported (Chem. Commun. 2007, 948) by Masakatsu Shibasaki of the University of Tokyo. Note that the free alcohol of 13 does not need to be protected.
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Taber, Douglass F. "The Tanino Synthesis of (-)-Glycinoeclepin A." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0095.

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(-)-Glycinoeclepin A 3 is effective at pg/mL concentrations as a hatch-stimulating agent for the soybean cyst nematode. Approaching the synthesis of 3, Keiji Tanino of Hokkaido University envisioned (Chemistry Lett. 2010, 39, 835) the convergent coupling of the allylic tosylate 2 with the bridgehead anion 1. The assembly of the fragment 2 was particularly challenging, because the synthesis would require not just the establishment of the two adjacent cyclic quaternary centers but also control of the relative configuration on the sidechain. The preparation of 1 began with the prochiral diketone 3. Enantioselective reduction of the mono enol ether 4 set the absolute configuration of 5. Iodination followed by cyclization then completed the assembly of 1. The construction of the bicyclic tosylate 2 began with m-methyl anisole 7. Following the Rubottom procedure, Birch reduction followed by mild hydrolysis gave the ketone 8. Epoxidation followed by β-elimination delivered the racemic 9, which was exposed to lipase to give, after seven days, the residual alcohol in 40% yield and high ee. The sidechain nitrile was prepared from the diol 12. Homologation gave the nitrile 14, which was equilibrated to the more stable enol ether 15. The two cyclic quaternary centers of 3 were set in a single step by the conjugate addition of the anion of 16 to the crystalline enone 11. Mild hydrolysis of 17 gave the keto aldehyde, which underwent aldol condensation to give the enone 18. The hydroboration of 19 followed by coupling of the intermediate organoborane with 20 delivered 21 with 94:6 relative diastereocontrol. Formylation of the enone 22 followed by triflation and reduction then led to 2. Altough the ketone 1 could be deprotonated with LDA, the only product observed, even at –78°C, was the derived aldol dimer. The metalated dimethylhydrazone 25, in contrast, coupled smoothly with 2 to give, after hydrolyis, the desired adduct 26. Pd-mediated carboxylation of the enol triflate followed by selective oxidative cleavage and hydrolysis then completed the synthesis of (-)-glycinoecleptin A 3.
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Taber, Douglass F. "Enantioselective Construction of Alkylated Centers: The Shishido Synthesis of (+)-Helianane." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0038.

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Teck-Peng Loh of Nanyang Technological University developed (Org. Lett. 2011, 13, 876) a catalyst for the enantioselective addition of an aldehyde to the versatile acceptor 2 to give 3. Kirsten Zeitler of the Universität Regensburg employed (Angew. Chem. Int. Ed. 2011, 50, 951) a complementary strategy for the enantioselective coupling of 4 with 5. Clark R. Landis of the University of Wisconsin devised (Org. Lett. 2011, 13, 164) an Rh catalyst for the enantioselective formylation of the diene 7. Don M. Coltart of Duke University alkylated (J. Am. Chem. Soc. 2011, 133, 8714) the chiral hydrazone of acetone to give 9, then alkylated again to give, after hydrolysis, the ketone 11 in high ee. Youming Wang and Zhenghong Zhou of Nankai University effected (J. Org. Chem. 2011, 76, 3872) the enantioselective addition of acetone to the nitroalkene 12. Takeshi Ohkuma of Hokkaido University achieved (Angew. Chem. Int. Ed. 2011, 50, 5541) high ee in the Ru-catalyzed hydrocyanation of 15. Gregory C. Fu, now at the California Institute of Technology, coupled (J. Am. Chem. Soc. 2011, 133, 8154) the 9-BBN borane 18 with the racemic chloride 17 to give 19 in high ee. Scott McN. Sieburth of Temple University optimized (Org. Lett. 2011, 13, 1787) an Rh catalyst for the enantioselective intramolecular hydrosilylation of 20 to 21. Several general methods have been devised for the enantioselective assembly of quaternary alkylated centers. Sung Ho Kang of KAIST Daejon developed (J. Am. Chem. Soc. 2011, 133, 1772) a Cu catalyst for the enantioselective acylation of the prochiral diol 22. Hyeung-geun Park of Seoul National University established (J. Am. Chem. Soc. 2011, 133, 4924) a phase transfer catalyst for the enantioselective alkylation of 24. Peter R. Schreiner of Justus-Liebig University Giessen found (J. Am. Chem. Soc. 2011, 133, 7624) a silicon catalyst that efficiently rearranged the Shi-derived epoxide of 26 to the aldehyde 27. Amir H. Hoveyda of Boston College coupled (J. Am. Chem. Soc. 2011, 133, 4778) 28 with the alkynyl Al reagent 29 to give 30 in high ee. Kozo Shishido of the University of Tokushima prepared (Synlett 2011, 1171) 31 by the Mitsunobu coupling of m-cresol with the enantiomerically pure allylic alcohol.
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Taber, Douglass. "Transition Metal Catalyzed Construction of Carbocyclic Rings: (-)-Hamigeran B." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0076.

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Several elegant methods for the enantioselective transformation of preformed prochiral rings have been put forward. Derek R. Boyd of Queen’s University, Belfast devised (Chem. Commun. 2008, 5535) a Cu catalyst that effected allylic oxidation of cyclic alkenes such as 1 with high ee. Christoph Jaekel of the Ruprecht-Karls-Universität Heidelberg established (Adv. Synth. Cat. 2008, 350, 2708) conditions for the enantioselective hydrogenation of cyclic enones such as 3. Marc L. Snapper of Boston College developed (Angew. Chem. Int. Ed. 2008, 47, 5049) a Cu catalyst for the enantioselective allylation of activated cyclic enones such as 5. Alexandre Alexakis of the University of Geneva showed (Angew. Chem. Int. Ed. 2008, 47, 9122) that dienones such as 8 could be induced to undergo 1,4 addition, again with high ee. Tsutomu Katsuki of Kyushu University originated (J. Am. Chem. Soc. 2008, 130, 10327) an Ir catalyst for the addition of diazoacetate 11 to alkenes such as 10 to give the cyclopropane 12 with high chemo-, enantio- and diastereoselectivity. Weiping Tang of the University of Wisconsin found (Angew. Chem. Int. Ed. 2008, 47, 8933) a silver catalyst that rearranged cyclopropyl diazo esters such as 13 to the cyclobutene 14 with high regioselectivity. Zhang-Jie Shi of Peking University demonstrated (J. Am. Chem. Soc. 2008, 130, 12901) that under oxidizing conditions, a Pd catalyst could cyclize 15 to 16. Sergio Castillón of the Universitat Rovira i Virgili, Tarragona devised (Organic Lett. 2008, 10, 4735) a Rh catalyst for the enantioselective cyclization of 17 to 18. Virginie Ratovelomanana-Vidal of the ENSCP Paris and Nakcheol Jeong of Korea University established (Adv. Synth. Cat. 2008, 350, 2695) conditions for the enantioselective intramolecular Pauson-Khand cyclization of 19 to give, after hydrolysis, the cyclopentenone 20. Quanrui Wang of Fudan University, Several elegant methods for the enantioselective transformation of preformed prochiral rings have been put forward. Derek R. Boyd of Queen’s University, Belfast devised (Chem. Commun. 2008, 5535) a Cu catalyst that effected allylic oxidation of cyclic alkenes such as 1 with high ee.
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Taber, Douglass F. "Organocatalytic C–C Ring Construction: Prostaglandin F2α (Aggarwal)." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0072.

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Marco Lombardo of the Università degli Studi di Bologna devised (Adv. Synth. Catal. 2012, 354, 3428) a silyl-bridged hydroxyproline catalyst that mediated the enantioselective addition of 2 to cinnamaldehyde 1 to give 3. Yoann Coquerel and Jean Rodriguez of Aix Marseille Université showed (Adv. Synth. Catal. 2012, 354, 3523) that a hybrid epi-cinchonine catalyst directed the enantioselective and diastereoselective addition of the amide 4 to the nitro alkene 5 to give 6. Magnus Rueping of RWTH Aachen observed (Angew. Chem. Int. Ed. 2012, 51, 12864) that a chiral Brønsted acid mediated the diastereoselective and enantioselective formation of 9 by the addition of 8 to cyclopentadiene 7. Marco Bandini, also of the University of Bologna, combined (Chem. Sci. 2012, 3, 2859) organocatalysis with gold catalysis to effect the cyclization of 10 to 11. Min Shi of the Shanghai Institute of Organic Chemistry prepared (Chem. Commun. 2012, 48, 2764) the quaternary cyclic amino acid derivative 14 by adding 13 to the acceptor 12. Makoto Tokunaga of Kyushu University prepared (Org. Lett. 2012, 14, 6178) the ketone 17 by the hydrolytic enantioselective protonation of the enol ester 15. Hiyoshizo Kotsuki of Kochi University developed (Synlett 2012, 23, 2554) a dual catalyst combination that effectively mediated the enantioselective addition of malonate even to the congested acceptor 18. Yoshitaka Hamashima and Toshiyuki Kan of the University of Shizuoka established (Org. Lett. 2012, 14, 6016) a protocol for the enantioselective brominative cyclization of 21, readily available by the reductive alkylation of benzoic acid. Polycarbocyclic ring systems can also be prepared by organocatalysis. Ying-Chun Chen of Sichuan University tuned (J. Am. Chem. Soc. 2012, 134, 19942) cinchona-derived catalysts to selectively convert 23 into either exo (illustrated) or endo 25. Peng-Fei Xu of Lanzhou University developed (Angew. Chem. Int. Ed. 2012, 51, 12339) a supramolecular iminium catalyst for the intramolecular Diels-Alder cycloaddition of 26. In a spectacular illustration of the power of organocatalysis, Varinder K. Aggarwal of the University of Bristol dimerized (Nature 2012, 489, 278) succinaldehyde from the hydrolysis of commercial 28 directly to the unsaturated aldehyde 29. Diastereoselective conjugate addition led to prostaglandin F2α 30.
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Taber, Douglass F. "Construction of Oxygenated and Aminated Stereogenic Centers." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0037.

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Computational analysis of the Novozyme 435 active site led (Tetrahedron Lett. 2010, 51, 309) Liyan Dai and Hongwei Yu of Zhejiang University, Hangzhou, to t-butanol for the enantioselective monoesterification of 1 to 2. Bruce H. Lipshutz of the University of California, Santa Barbara, devised (J. Am. Chem. Soc. 2010, 132, 7852) a Cu catalyst that mediated the enantioselective 1,2-reduction of α-branched enones such as 3. Qi-Lin Zhou of Nankai University found (J. Am. Chem. Soc. 2010, 132, 1172) that an α-alkoxy unsaturated acid 5 could be hydrogenated with high ee. Tohru Yamada of Keio University desymmetrized (J. Am. Chem. Soc. 2010, 132, 4072) the tertiary alcohol 7, delivering the enol lactone 8. Zachary D. Aron of Indiana University established (Organic Lett. 2010, 12, 1916) that the simple aldehyde 10 effected rapid racemization of the α-amino ester 9. Running the epimerization in the presence of an enantioselective esterase produced 11 high ee. Robert A. Batey of the University of Toronto devised (Organic Lett. 2010, 12, 260) a Pd catalyst for the enantioselective rearrangement of 12 to 13. In the course of a synthesis of dapoxetine, Hyeon-Kyu Lee of the Korea Research Institute of Chemical Technology showed (J. Org. Chem. 2010, 75, 237) that the Rh*-mediated intramolecular C-H insertion of 14 to 15, as developed by Du Bois, gave the opposite absolute configuration to that originally assigned. To prepare α-quaternary amines, Thomas G. Back of the University of Calgary explored (J. Org. Chem. 2010, 75, 1612) the selectivity of the PLE hydrolysis of esters such as 16. Daniel R. Fandrick and colleagues at Boehringer Ingelheim reported (J. Am. Chem. Soc. 2010, 132, 7600) a general method for the catalytic enantioselective propargylation of aldehydes, including 18. Dennis G. Hall of the University of Alberta devised (J. Am. Chem. Soc. 2010, 132, 5544) a route to α-hydroxy esters such as 22 by enantioselective conjugate addition to 21. Alexandre Alexakis of the University of Geneva prepared (Chem. Commun. 2010, 46, 4085) disubstituted epoxides such as 25 by the conjugate addition of 23 to 24.
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10

Olejniczak, Teresa, and Czesŀaw Wawrzeńczyk. "Lactones 8. [1] Enantioselective hydrolysis of γ-acetoxy-δ-lactones." In Studies in Surface Science and Catalysis, 3387–92. Elsevier, 2000. http://dx.doi.org/10.1016/s0167-2991(00)80546-7.

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Conference papers on the topic "Enantioselective hydrolyses"

1

Sato, Letícia, Paulo José Samenho Moran, Lucidio Cristovão Fardelone, and José Augusto Rosário Rodrigues. "Screening of Lipases for Enantioselective Hydrolysis of 1-butiryloxyarylphosphonates." In XXIV Congresso de Iniciação Científica da UNICAMP - 2016. Campinas - SP, Brazil: Galoa, 2016. http://dx.doi.org/10.19146/pibic-2016-51226.

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2

Gao, Shengbo, Quanhui Li, Tingting Yao, Zhengyang Wang, Luoyun Zheng, and Jiaying Xin. "Lipase Catalyzed Naproxen Methyl Ester Enantioselective Hydrolysis in Ionic Liquids." In 2016 6th International Conference on Mechatronics, Computer and Education Informationization (MCEI 2016). Paris, France: Atlantis Press, 2016. http://dx.doi.org/10.2991/mcei-16.2016.4.

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3

Zhang, Chensheng, Zhijun Zhang, Chunxiu Li, Huilei Yu, and Jianhe Xu. "Enantioselective Hydrolysis of O-Chloromandelonitrile by Novel Arylacetonitrilase Mined from Gene Database." In 14th Asia Pacific Confederation of Chemical Engineering Congress. Singapore: Research Publishing Services, 2012. http://dx.doi.org/10.3850/978-981-07-1445-1_324.

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4

SANTOS DE OLIVEIRA, PRISCILA, Paulo José Samenho Moran, Lucidio Cristovão Fardelone, and José Augusto Rosário Rodrigues. "Enantioselective Hydrolysis of 1-Aryl-2-chloroethyl propanoate Mediated by Burkholderia cepacia and Candida rugosa Lipases." In XXIV Congresso de Iniciação Científica da UNICAMP - 2016. Campinas - SP, Brazil: Galoa, 2016. http://dx.doi.org/10.19146/pibic-2016-50943.

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