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Journal articles on the topic 'Enantioselective'

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Author: Grafiati

Published: 4 June 2021

Last updated: 7 July 2024

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1

Gualandi, Andrea, Luca Mengozzi, and Pier Cozzi. "Stereoselective SN1-Type Reaction of Enols and Enolates." Synthesis 49, no. 15 (June 13, 2017): 3433–43. http://dx.doi.org/10.1055/s-0036-1588871.

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Stereoselective alkylation of enolates represents a valuable and important procedure for accessing carbon–carbon-bond frameworks in natural and nonnatural product synthesis. Usually, activated electrophilic partners that react through an SN2 mechanism are employed. To overcome the limitations due to reduced reactivity and steric hindrance, SN1-type reactions can be considered a valid and practical alternative. Accessible enolates can be used in stereoselective (diastereo- or enantioselective) reactions with electrophilic carbenium ions, either used as stable reagents or generated in situ from suitable precursors. The results achieved in this active field are summarized in this review.1 Introduction2 Alcohols in SN1-Type Reactions with Enolates2.1 Enantioselective Reactions with Metal Complexes2.2 Organocatalytic Enantioselective Reactions3 Alcohols and Alcohol Derivatives in SN1-Type Reactions with Enolates: Enantioselective Reactions with Metal Enolates4 Isolated Carbenium Ions in SN1-Type Reactions with Enolates: Enantioselective Reactions with Metal Enolates5 Miscellaneous6 Conclusion

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2

Zhang, Yafeng, Huizhen Wang, Hu Yu, and Xiaoxia Sun. "Chiral fluorescent sensor based on H₈-BINOL for the high enantioselective recognition of d- and l-phenylalanine." RSC Advances 12, no. 19 (2022): 11967–73. http://dx.doi.org/10.1039/d2ra00803c.

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A triazole-modified H8-BINOL fluorescence sensor was synthesized with 95% yield, which can enantioselectively recognize l-phenylalanine without the participation of metal ions, even the enantioselective fluorescence enhancement ratio was up to 104.28.

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3

Jakob, Bastian, Nico Schneider, Luca Gengenbach, and Georg Manolikakes. "Palladium-catalyzed enantioselective three-component synthesis of α-arylglycine derivatives from glyoxylic acid, sulfonamides and aryltrifluoroborates." Beilstein Journal of Organic Chemistry 19 (May 25, 2023): 719–26. http://dx.doi.org/10.3762/bjoc.19.52.

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A palladium-catalyzed enantioselective three-component reaction of glyoxylic acid, sulfonamides and aryltrifluoroborates is described. This process provides modular access to the important α-arylglycine motif in moderate to good yields and enantioselectivies. The formed α-arylglycine products constitute useful building blocks for the synthesis of peptides or arylglycine-containing natural products.

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4

He, Chuan, and Wei Yuan. "Enantioselective C–H Functionalization toward Silicon-Stereogenic Silanes." Synthesis 54, no. 08 (January 3, 2022): 1939–50. http://dx.doi.org/10.1055/a-1729-9664.

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AbstractIn recent years, transition-metal-catalyzed enantioselective C–H bond functionalization has emerged as a powerful and attractive synthetic approach to access silicon-stereogenic centers, which provides impetus for the innovation of chiral organosilicon chemistry. This short review summarizes recent advances in the construction of silicon-stereogenic silanes via transition-metal-catalyzed enantioselective C–H functionalization. We endeavor to highlight the great potential of this methodology and hope that this review will shed light on new perspectives and inspire further research in this emerging area.1 Introduction2 Enantioselective C–H Functionalization Induced by Oxidative Addition of an Aryl-OTf Bond3 Enantioselective C–H Functionalization Induced by Oxidative Addition of a Silacyclobutane4 Directing-Group-Assisted Enantioselective C–H Functionalization5 Enantioselective Dehydrogenative C–H/Si–H Coupling5.1 Enantioselective C(sp2)–H Silylation5.2 Enantioselective C(sp3)–H Silylation6 Summary and Outlook

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5

Gong, Liu-Zhu, Pu-Sheng Wang, and Meng-Lan Shen. "Transition-Metal-Catalyzed Asymmetric Allylation of Carbonyl Compounds with Unsaturated Hydrocarbons." Synthesis 50, no. 05 (December 21, 2017): 956–67. http://dx.doi.org/10.1055/s-0036-1590986.

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The asymmetric allylation of carbonyl compounds is an important process for the formation of carbon–carbon bonds, generating optically active homoallylic alcohols that are versatile building blocks with widespread applications in organic synthesis. The use of readily available unsaturated hydrocarbons as allylating reagents in the transition-metal-catalyzed asymmetric allylation has received increasing interest as either a step- or an atom-economy alternative. This review summarizes transition-metal-catalyzed enantioselective allylations on the basis of the ‘indirect’ and ‘direct’ use of simple unsaturated hydrocarbons (include dienes, allenes, alkynes, and alkenes) as allylating reagents, with emphasis on highlighting conceptually novel reactions.1 Introduction2 ‘Indirect’ Use of Unsaturated Hydrocarbons in Asymmetric Allylation of Carbonyl Compounds2.1 Enantioselective Allylation with 1,3-Dienes2.2 Enantioselective Allylation with Allenes2.3 Enantioselective Allylation with Alkenes3 ‘Direct’ Use of Unsaturated Hydrocarbons in Asymmetric Allylation of Carbonyl Compounds3.1 Enantioselective Allylation with 1,3-Dienes3.2 Enantioselective Allylation with Allenes3.3 Enantioselective Allylation with Alkynes3.4 Enantioselective Allylation with Alkenes4 Conclusions

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6

Bower, John F., Timothy P. Aldhous, Raymond W. M. Chung, and Andrew G. Dalling. "Enantioselective Intermolecular Murai-Type Alkene Hydroarylation Reactions." Synthesis 53, no. 17 (May 25, 2021): 2961–75. http://dx.doi.org/10.1055/s-0040-1720406.

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AbstractStrategies that enable the efficient assembly of complex building blocks from feedstock chemicals are of paramount importance to synthetic chemistry. Building upon the pioneering work of Murai and co-workers in 1993, C–H-activation-based enantioselective hydroarylations of alkenes offer a particularly promising framework for the step- and atom-economical installation of benzylic stereocenters. This short review presents recent intermolecular enantioselective Murai-type alkene hydroarylation methodologies and the mechanisms by which they proceed.1 Introduction2 Enantioselective Hydroarylation Reactions of Strained Bicyclic Alkenes3 Enantioselective Hydroarylation Reactions of Electron-Rich Acyclic Alkenes4 Enantioselective Hydroarylation Reactions of Electron-Poor Acyclic Alkenes5 Enantioselective Hydroarylation Reactions of Minimally Polarized Acyclic Alkenes6 Conclusion and Outlook

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7

Cozzi, Pier Giorgio, Alessandro Mignogna, and Luca Zoli. "Catalytic enantioselective Reformatsky reactions." Pure and Applied Chemistry 80, no. 5 (January 1, 2008): 891–901. http://dx.doi.org/10.1351/pac200880050891.

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The Reformatsky reaction is a venerable named reaction that was introduced more than 120 years ago. Diastereoselective variants based on the use of chiral auxiliary and enantioselective protocols, based on the employment of stoichiometric amount of chiral ligands, have been successfully applied in organic synthesis during the years. However, a facile and general catalytic enantioselective variant was still a difficult task. Recently, we have established a new general and straightforward methodology for catalytic enantioselective Reformatsky reaction based on different concepts. In this paper, we present our general finding in catalytic enantioselective Reformatsky reaction of ketones, imines, and aldehydes. Our simple methodologies could become benchmark reactions for testing new synthesized chiral ligands for asymmetric transformations.

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8

Brüllingen, Eric, Jörg-Martin Neudörfl, and Bernd Goldfuss. "Enantioselective Cu-catalyzed 1,4-additions of organozinc and Grignard reagents to enones: exceptional performance of the hydrido-phosphite-ligand BIFOP-H." New Journal of Chemistry 43, no. 12 (2019): 4787–99. http://dx.doi.org/10.1039/c8nj05886e.

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9

Boussonnière, Anne, Anne-Sophie Castanet, and Hélène Guyon. "Transition-Metal-Free Enantioselective Reactions of Organomagnesium Reagents Mediated by Chiral Ligands." Synthesis 50, no. 18 (June 20, 2018): 3589–602. http://dx.doi.org/10.1055/s-0037-1610135.

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Organomagnesium reagents are among the most important reagents in organic chemistry because of their great utility in forming carbon–carbon bonds. Although most enantioselective reactions using these organometallics involve transmetalation, the past decade has witnessed impressive advances in direct chiral-ligand-mediated reactions of organomagnesiums. This short review presents an overview of these achievements in enantioselective nucleophilic additions and substitutions.1 Introduction2 Enantioselective Nucleophilic Additions2.1 Addition to C=O Bonds2.2 Addition to C=N Bonds2.3 Addition to C=C Bonds3 Enantioselective Substitution Reactions3.1 Sulfoxide–Magnesium Exchange3.2 Desymmetrization via Anhydride Opening3.3 Asymmetric Allylic Alkylation (AAA)4 Conclusion

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10

Shukla, Nisha, Zachary Blonder, and Andrew J. Gellman. "Chiral Separation of rac-Propylene Oxide on Penicillamine Coated Gold NPs." Nanomaterials 10, no. 9 (August 30, 2020): 1716. http://dx.doi.org/10.3390/nano10091716.

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The surfaces of chemically synthesized spherical gold NPs (Au-NPs) have been modified using chiral L- or D-penicillamine (Pen) in order to impart enantioselective adsorption properties. These chiral Au-NPs have been used to demonstrate enantioselective adsorption of racemic propylene oxide (PO) from aqueous solution. In the past we have studied enantioselective adsorption of racemic PO on L- or D-cysteine (Cys)-coated Au-NPs. This prior work suggested that adsorption of PO on Cys-coated Au-NPs equilibrates within an hour. In this work, we have studied the effect of time on the enantioselective adsorption of racemic PO from solution onto chiral Pen/Au-NPs. Enantioselective adsorption of PO on chiral Pen/Au-NPs is time-dependent but reaches a steady state after ~18 h at room temperature. More importantly, L- or D-Pen/Au-NPs are shown to adsorb R- or S-PO enantiospecifically and to separate the two PO enantiomers from racemic mixtures of RS-PO.

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11

Fontana, Francesca, Greta Carminati, Benedetta Bertolotti, Patrizia Romana Mussini, Serena Arnaboldi, Sara Grecchi, Roberto Cirilli, Laura Micheli, and Simona Rizzo. "Helicity: A Non-Conventional Stereogenic Element for Designing Inherently Chiral Ionic Liquids for Electrochemical Enantiodifferentiation." Molecules 26, no. 2 (January 9, 2021): 311. http://dx.doi.org/10.3390/molecules26020311.

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Configurationally stable 5-aza[6]helicene (1) was envisaged as a promising scaffold for non-conventional ionic liquids (IL)s. It was prepared, purified, and separated into enantiomers by preparative HPLC on a chiral stationary phase. Enantiomerically pure quaternary salts of 1 with appropriate counterions were prepared and fully characterized. N-octyl-5-aza[6]helicenium bis triflimidate (2) was tested in very small quantities as a selector in achiral IL media to perform preliminary electrochemical enantiodifferentiation experiments on the antipodes of two different chiral probes. The new organic salt exhibited outstanding enantioselection performance with respect to these probes, thus opening the way to applications in the enantioselective electroanalysis of relevant bioactive molecules.

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12

Fontana, Francesca, Greta Carminati, Benedetta Bertolotti, Patrizia Romana Mussini, Serena Arnaboldi, Sara Grecchi, Roberto Cirilli, Laura Micheli, and Simona Rizzo. "Helicity: A Non-Conventional Stereogenic Element for Designing Inherently Chiral Ionic Liquids for Electrochemical Enantiodifferentiation." Molecules 26, no. 2 (January 9, 2021): 311. http://dx.doi.org/10.3390/molecules26020311.

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Configurationally stable 5-aza[6]helicene (1) was envisaged as a promising scaffold for non-conventional ionic liquids (IL)s. It was prepared, purified, and separated into enantiomers by preparative HPLC on a chiral stationary phase. Enantiomerically pure quaternary salts of 1 with appropriate counterions were prepared and fully characterized. N-octyl-5-aza[6]helicenium bis triflimidate (2) was tested in very small quantities as a selector in achiral IL media to perform preliminary electrochemical enantiodifferentiation experiments on the antipodes of two different chiral probes. The new organic salt exhibited outstanding enantioselection performance with respect to these probes, thus opening the way to applications in the enantioselective electroanalysis of relevant bioactive molecules.

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13

Cai, Quan, Xu-Ge Si, and Zhi-Mao Zhang. "Asymmetric Inverse-Electron-Demand Diels–Alder Reactions of 2-Pyrones by Lewis Acid Catalysis." Synlett 32, no. 10 (January 24, 2021): 947–54. http://dx.doi.org/10.1055/a-1371-4391.

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AbstractDiels–Alder reactions of 2-pyrones with alkenes can provide highly functionalized [2,2,2]-bicyclic lactones under mild reaction conditions. Synthetic utilizations of these reactions have been well demonstrated in natural-product synthesis. Although several catalytic asymmetric strategies have been realized, current research in this area is still largely underdeveloped. Recent advances in enantioselective inverse-electron-demand Diels–Alder reactions with Lewis acid catalysis are reviewed.1 Introduction2 State of the Art of Enantioselective Diels–Alder Reactions of 2-Pyrones by Lewis Acid Catalysis3 Enantioselective Synthesis of Arene cis-Dihydrodiols by Diels–Alder/Retro-Diels–Alder Reactions of 2-Pyrones4 Enantioselective Synthesis of cis-Decalin Derivatives by Diels–Alder Reactions of 2-Pyrones5 Conclusions

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14

Meyer, Timo, Nadine Zumbrägel, Christina Geerds, Harald Gröger, and Hartmut H. Niemann. "Structural Characterization of an S-enantioselective Imine Reductase from Mycobacterium Smegmatis." Biomolecules 10, no. 8 (July 31, 2020): 1130. http://dx.doi.org/10.3390/biom10081130.

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NADPH-dependent imine reductases (IREDs) are enzymes capable of enantioselectively reducing imines to chiral secondary amines, which represent important building blocks in the chemical and pharmaceutical industry. Since their discovery in 2011, many previously unknown IREDs have been identified, biochemically and structurally characterized and categorized into families. However, the catalytic mechanism and guiding principles for substrate specificity and stereoselectivity remain disputed. Herein, we describe the crystal structure of S-IRED-Ms from Mycobacterium smegmatis together with its cofactor NADPH. S-IRED-Ms belongs to the S-enantioselective superfamily 3 (SFam3) and is the first IRED from SFam3 to be structurally described. The data presented provide further evidence for the overall high degree of structural conservation between different IREDs of various superfamilies. We discuss the role of Asp170 in catalysis and the importance of hydrophobic amino acids in the active site for stereospecificity. Moreover, a separate entrance to the active site, potentially functioning according to a gatekeeping mechanism regulating access and, therefore, substrate specificity is described.

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15

Du, Kang, He Yang, Pan Guo, Liang Feng, Guangqing Xu, Qinghai Zhou, Lung Wa Chung, and Wenjun Tang. "Efficient syntheses of (−)-crinine and (−)-aspidospermidine, and the formal synthesis of (−)-minfiensine by enantioselective intramolecular dearomative cyclization." Chemical Science 8, no. 9 (2017): 6247–56. http://dx.doi.org/10.1039/c7sc01859b.

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Palladium-catalyzed enantioselective dearomative cyclization has enabled the concise and enantioselective total syntheses of (−)-crinine and (−)-aspidospermidine, as well as a formal total synthesis of (−)-minfiensine.

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16

Susanti, Asep Riswoko, Joddy Arya Laksmono, Galuh Widiyarti, and Dadan Hermawan. "Surface modified nanoparticles and their applications for enantioselective detection, analysis, and separation of various chiral compounds." RSC Advances 13, no. 26 (2023): 18070–89. http://dx.doi.org/10.1039/d3ra02399k.

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The combination of surface-modified nanomaterials and chiral selectors can improve enantioselective recognition with a significant influence on the performance of enantioselective detection, analysis, and separation.

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17

Ungarean, Chad N., Emma H. Southgate, and David Sarlah. "Enantioselective polyene cyclizations." Organic & Biomolecular Chemistry 14, no. 24 (2016): 5454–67. http://dx.doi.org/10.1039/c6ob00375c.

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18

Liu, Juan, Soumya Mukherjee, Fei Wang, Roland A. Fischer, and Jian Zhang. "Homochiral metal–organic frameworks for enantioseparation." Chemical Society Reviews 50, no. 9 (2021): 5706–45. http://dx.doi.org/10.1039/d0cs01236j.

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Contextualising rational structural design, according to the enantioselective mechanisms of homochiral metal–organic frameworks, we discuss enantioselective separations primed to deliver purification performances and analytical utilities thereof.

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19

Stoltz, Brian, Christian Defieber, Justin Mohr, and Gennadii Grabovyi. "Short Enantioselective Formal Synthesis of (–)-Platencin." Synthesis 50, no. 22 (July 23, 2018): 4359–68. http://dx.doi.org/10.1055/s-0037-1610437.

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A short enantioselective formal synthesis of the antibiotic natural product platencin is reported. Key steps in the synthesis include enantioselective decarboxylation alkylation, aldehyde/olefin radical cyclization, and regioselective aldol cyclization.

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20

Wang, Gang, Shutao Sun, Ying Mao, Zhiyu Xie, and Lei Liu. "Chromium(II)-catalyzed enantioselective arylation of ketones." Beilstein Journal of Organic Chemistry 12 (December 19, 2016): 2771–75. http://dx.doi.org/10.3762/bjoc.12.275.

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The chromium-catalyzed enantioselective addition of carbo halides to carbonyl compounds is an important transformation in organic synthesis. However, the corresponding catalytic enantioselective arylation of ketones has not been reported to date. Herein, we report the first Cr-catalyzed enantioselective addition of aryl halides to both arylaliphatic and aliphatic ketones with high enantioselectivity in an intramolecular version, providing facile access to enantiopure tetrahydronaphthalen-1-ols and 2,3-dihydro-1H-inden-1-ols containing a tertiary alcohol.

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21

Huang, Xiao-Huan, Yong-Bing He, Zhi-Hong Chen, Chen-Guang Hu, and Guang-Yan Qing. "Novel chiral fluorescent chemosensors for malate and acidic amino acids based on two-arm thiourea and amide." Canadian Journal of Chemistry 86, no. 2 (February 1, 2008): 170–76. http://dx.doi.org/10.1139/v07-147.

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The charge neutral anthracene based chiral fluorescent receptors 4a and 4b containing thiourea and amide groups were synthesized by simple steps in good yields, and their enantioselective recognition for chiral dicarboxylic anions (L/D-malate, L/D-aspartate, and L/D-glutamate) were examined by UV–vis, fluorescence, and 1H NMR spectroscopy. The sensor 4a exhibited an excellent enantioselective recognition ability towards malate (Kass (L)/Kass (D) = 9.65).Key words: enantioselective recognition, chiral chemosensor, fluorescence, malate.

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22

Reynolds, Rebekah G., Huong Quynh Anh Nguyen, Jordan C. T. Reddel, and Regan J. Thomson. "Recent strategies and tactics for the enantioselective total syntheses of cyclolignan natural products." Natural Product Reports 39, no. 3 (2022): 670–702. http://dx.doi.org/10.1039/d1np00057h.

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This review highlights strategies for the enantioselective total synthesis of cyclolignan natural products from 2000 to 2021. Each subsection focuses on the key strategic disconnections and the enantioselective steps controlling asymmetric induction.

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23

Wu, Wang, Zhang, and Jin. "Urea-Derivative Catalyzed Enantioselective Hydroxyalkylation of Hydroxyindoles with Isatins." Molecules 24, no. 21 (October 31, 2019): 3944. http://dx.doi.org/10.3390/molecules24213944.

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The enantioselective transformations of indoles preferentially take place in the more-reactive azole ring. However, the methods for the enantioselective functionalization of the indole benzene ring are scarce. In this paper, a series of bifunctional (thio)urea derivatives were used to organocatalyze the enantioselective Friedel−Crafts hydroxyalkylation of indoles with isatins. The resulting products were obtained in good yields (65–90%) with up to 94% enantiomer excess (ee). The catalyst type and the substrate scope were broadened in this methodology.

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24

Li, Chengxi, Sherif Shaban Ragab, Guodu Liu, and Wenjun Tang. "Enantioselective formation of quaternary carbon stereocenters in natural product synthesis: a recent update." Natural Product Reports 37, no. 2 (2020): 276–92. http://dx.doi.org/10.1039/c9np00039a.

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The enantioselective formation of quaternary carbon stereocenters in complex natural product synthesis in the latest six years is reviewed, with particular emphasis on the analysis of the stereochemical model of each enantioselective transformation.

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25

Zhou, Zhijun, Sheng Xu, Jing Zhang, and Wangqing Kong. "Nickel-catalyzed enantioselective electroreductive cross-couplings." Organic Chemistry Frontiers 7, no. 20 (2020): 3262–65. http://dx.doi.org/10.1039/d0qo00901f.

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Ni-Catalyzed reductive cross-coupling of two electrophiles has evolved into a powerful means for building diverse carbon-carbon bonds in an enantioselective manner. Here we summarize the recent progress in Ni-catalyzed enantioselective electroreductive coupling reactions.

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26

FUJI, Kaoru. "Enantioselective reactions." Journal of Synthetic Organic Chemistry, Japan 44, no. 7 (1986): 623–32. http://dx.doi.org/10.5059/yukigoseikyokaishi.44.623.

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27

Kahr, Bart, and Alexander G. Shtukenberg. "Enantioselective photoactivation." Nature Materials 14, no. 1 (December 17, 2014): 21–22. http://dx.doi.org/10.1038/nmat4174.

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28

Lee, Ai-Lan. "Enantioselective catalysis." Annual Reports Section "B" (Organic Chemistry) 105 (2009): 421. http://dx.doi.org/10.1039/b905117c.

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29

C. Willis, Michael. "Enantioselective desymmetrisation." Journal of the Chemical Society, Perkin Transactions 1, no. 13 (1999): 1765. http://dx.doi.org/10.1039/a906269b.

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30

STINSON, STEPHEN C. "ENANTIOSELECTIVE CHEMISTRY." Chemical & Engineering News 75, no. 17 (April 28, 1997): 26–27. http://dx.doi.org/10.1021/cen-v075n017.p026.

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31

He, Huarui, Georg Uray, and Otto S. Wolfbeis. "Enantioselective optodes." Analytica Chimica Acta 246, no. 2 (June 1991): 251–57. http://dx.doi.org/10.1016/s0003-2670(00)80958-7.

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32

Brunner, Henri, and Christian Krumey. "Enantioselective catalysis." Journal of Molecular Catalysis A: Chemical 142, no. 1 (May 1999): 7–15. http://dx.doi.org/10.1016/s1381-1169(98)00283-0.

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33

Brunner, Henri, Matthias Weber, and Manfred Zabel. "Enantioselective catalysis." Journal of Organometallic Chemistry 684, no. 1-2 (November 2003): 6–12. http://dx.doi.org/10.1016/s0022-328x(03)00224-9.

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34

Brunner, Henri, and Darijo Mijolovic. "Enantioselective catalysis." Journal of Organometallic Chemistry 577, no. 2 (April 1999): 346–50. http://dx.doi.org/10.1016/s0022-328x(98)01082-1.

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35

Brunner, Henri, Andreas Winter, and Josef Breu. "Enantioselective catalysis." Journal of Organometallic Chemistry 553, no. 1-2 (February 1998): 285–306. http://dx.doi.org/10.1016/s0022-328x(97)00570-6.

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36

Mohr, Justin T., Allen Y. Hong, and Brian M. Stoltz. "Enantioselective protonation." Nature Chemistry 1, no. 5 (July 24, 2009): 359–69. http://dx.doi.org/10.1038/nchem.297.

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37

Lee, Ai-Lan. "Enantioselective catalysis." Annual Reports Section "B" (Organic Chemistry) 107 (2011): 369. http://dx.doi.org/10.1039/c1oc90001c.

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38

Lee, Ai-Lan. "Enantioselective catalysis." Annual Reports Section "B" (Organic Chemistry) 106 (2010): 428. http://dx.doi.org/10.1039/b927080a.

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39

Ward, Dale E., and Wan-Li Lu. "Enantioselective Enolborination." Journal of the American Chemical Society 120, no. 5 (February 1998): 1098–99. http://dx.doi.org/10.1021/ja973686c.

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40

Keim, Wilhelm, Angela Koehnes, Thomas Roethel, and Dieter Enders. "Enantioselective telomerization." Journal of Organometallic Chemistry 382, no. 1-2 (February 1990): 295–301. http://dx.doi.org/10.1016/0022-328x(90)85233-o.

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41

Slipszenko, J. A., S. P. Griffiths, P. Johnston, K. E. Simons, W. A. H. Vermeer, and P. B. Wells. "Enantioselective Hydrogenation." Journal of Catalysis 179, no. 1 (October 1998): 267–76. http://dx.doi.org/10.1006/jcat.1998.2204.

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42

Gaunt, Matthew J., Carin C. C. Johansson, Andy McNally, and Ngoc T. Vo. "Enantioselective organocatalysis." Drug Discovery Today 12, no. 1-2 (January 2007): 8–27. http://dx.doi.org/10.1016/j.drudis.2006.11.004.

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43

Simons, K. E., A. Ibbotson, P. Johnston, H. Plum, and P. B. Wells. "Enantioselective Hydrogenation." Journal of Catalysis 150, no. 2 (December 1994): 321–28. http://dx.doi.org/10.1006/jcat.1994.1350.

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44

Bond, G., and P. B. Wells. "Enantioselective Hydrogenation." Journal of Catalysis 150, no. 2 (December 1994): 329–34. http://dx.doi.org/10.1006/jcat.1994.1351.

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45

Dalko, Peter I., and Lionel Moisan. "Enantioselective Organocatalysis." Angewandte Chemie International Edition 40, no. 20 (October 15, 2001): 3726–48. http://dx.doi.org/10.1002/1521-3773(20011015)40:20<3726::aid-anie3726>3.0.co;2-d.

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46

Hutchings, Graham J. "Enantioselective catalysis." Applied Catalysis A: General 91, no. 1 (November 1992): N4. http://dx.doi.org/10.1016/0926-860x(92)85180-j.

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47

Xue, Moyong, Xu Gu, Yuchang Qin, Junguo Li, Qingshi Meng, and Ming Jia. "Enantioselective Behavior of Flumequine Enantiomers and Metabolites’ Identification in Sediment." Journal of Analytical Methods in Chemistry 2022 (December 2, 2022): 1–12. http://dx.doi.org/10.1155/2022/2184024.

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The enantioselective adsorption, degradation, and transformation of flumequine (FLU) enantiomers in sediment were investigated to elucidate the enantioselective environmental behaviors. The results of adsorption test showed that stereoselective differences of FLU enantiomers in sediment samples and the adsorbing capacity of S-(−)-FLU and R-(+)-FLU are higher than the racemate, and the pH values of the sediment determined the adsorption capacity. Enantioselective degradation behaviors were found under nonsterilized conditions and followed pseudo-first-order kinetic. The R-(+)-FLU was preferentially degraded, and there was significant enantioselectivity of the degradation of FLU. It can be concluded that the microorganism was the main reason for the stereoselective degradation in sediments. The physicochemical property of sediments, such as pH value and organic matter content, can affect the degradation rate of FLU. In addition, the process of transformation of FLU enantiomers in water-sediment system had enantioselective behavior, and R-(+)-FLU was preferential transformed. Meanwhile, the main metabolites of FLU in the sediment were decarboxylate and dihydroxylation products. This study contributes the evidence of comprehensively assessing the fate and risk of chiral FLU antibiotic and enantioselective behavior in the environment.

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Segovia, Claire, Arthur Lebrêne, Vincent Levacher, Sylvain Oudeyer, and Jean-François Brière. "Enantioselective Catalytic Transformations of Barbituric Acid Derivatives." Catalysts 9, no. 2 (February 1, 2019): 131. http://dx.doi.org/10.3390/catal9020131.

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Since the beginning of the 20th century, numerous research efforts made elegant use of barbituric acid derivatives as building blocks for the elaboration of more complex and useful molecules in the field of pharmaceutical chemistry and material sciences. However, the construction of chiral scaffolds by the catalytic enantioselective transformation of barbituric acid and derivatives has only emerged recently. The specific properties of these rather planar scaffolds, which also encompass either a high Brønsted acidity concerning the native barbituric acid or the marked electrophilic character of alkylidene barbituric acids, required specific developments to achieve efficient asymmetric processes. This review covers the enantioselective catalytic reactions developed for barbituric acid platforms using an organocatalytic and metal-based enantioselective sequences. These achievements currently allow several unique addition and annulation reactions towards the construction of high valued chiral heterocycles from barbituric acid derivatives along with innovative enantioselective developments.

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Zhang, Guoting, Matthew D. Wodrich, and Nicolai Cramer. "Catalytic enantioselective reductive Eschenmoser-Claisen rearrangements." Science 383, no. 6681 (January 26, 2024): 395–401. http://dx.doi.org/10.1126/science.adl3369.

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An important challenge in enantioselective catalysis is developing strategies for the precise synthesis of neighboring congested all-carbon quaternary stereocenters. The well-defined transition states of [3,3]-sigmatropic rearrangements and their underlying stereospecificity render them powerful tools for the synthesis of such arrays. However, this type of pericyclic reaction remains notoriously difficult to catalyze, especially in an enantioselective fashion. Herein, we describe an enantioselective reductive Eschenmoser-Claisen rearrangement catalyzed by chiral 1,3,2-diazaphospholene-hydrides. This developed transformation enables full control of the two newly formed acyclic stereogenic centers, leading to amides with vicinal all-carbon quaternary-tertiary or quaternary-quaternary carbon atoms.

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Wang, Guo-Peng, Meng-Qing Chen, Shou-Fei Zhu, and Qi-Lin Zhou. "Enantioselective Nazarov cyclization of indole enones cooperatively catalyzed by Lewis acids and chiral Brønsted acids." Chemical Science 8, no. 10 (2017): 7197–202. http://dx.doi.org/10.1039/c7sc03183a.

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The first enantioselective Nazarov cyclization of substrates with only one coordinating site and with proton-transfer as an enantioselective-determining step was realized by means of cooperative catalysis with a Lewis acid and a chiral Brønsted acid.

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