Relevant bibliographies by topics / Chiral Lewis acid

Academic literature on the topic 'Chiral Lewis acid'

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Published: 4 June 2021
Last updated: 19 February 2022

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Journal articles on the topic "Chiral Lewis acid"

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Kim, Yong Hae, Doo Young Jung, So Won Youn, Sam Min Kim, and Doo Han Park. "Dual enantioselective control by heterocycles of (S)-indoline derivatives." Pure and Applied Chemistry 77, no. 12 (January 1, 2005): 2053–59. http://dx.doi.org/10.1351/pac200577122053.

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Diastereo-and enantioselective pinacol coupling reactions of chiral α-ketoamides mediated by samarium diiodide afforded extremely high diastereoselectivities. Enantiopure (S,S)- or (R,R)-2,3-dialkyltartaric acid and derivatives can be synthesized. Diels-Alder cycloadditions of S-indoline chiral acrylamides with cyclopentadiene in the presence of Lewis acids proceed with high diastereofacial selectivity, giving either endo-R or endo-S products depending on Lewis acid and the structures of chiral dienophiles.
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Kim, Yong Hae, Sam Min Kim, and So Won Youn. "Asymmetric synthesis by stereocontrol." Pure and Applied Chemistry 73, no. 2 (January 1, 2001): 283–86. http://dx.doi.org/10.1351/pac200173020283.

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Diels-Alder cycloadditions of S-indoline chiral acrylamides with cyclopentadiene in the presence of Lewis acids proceed with high diastereofacial selectivity, giving either endo-R or endo-S products depending on Lewis acid and the structures of chiral dienophiles. Diastereo- and enantioselective pinacol coupling reactions of chiral α-ketoamides mediated by samarium diiodide afforded extremely high diastereoselectivities. Enantiopure (S,S) - or (R,R) -2,3-dialkyltartaric acid and derivatives can be synthesized. Furthermore, it was demonstrated that α,β-unsaturated amides coupled with SmI2 to dimerized products containing two chiral carbons which were first obtained as the adjacent chiral carbons.
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Cantú-Reyes, Margarita, Isabel Alvarado-Beltrán, Ricardo Ballinas-Indilí, Cecilio Álvarez-Toledano, and Marcos Hernández-Rodríguez. "Stereodivergent Mannich reaction of bis(trimethylsilyl)ketene acetals with N-tert-butanesulfinyl imines by Lewis acid or Lewis base activation, a one-pot protocol to obtain chiral β-amino acids." Organic & Biomolecular Chemistry 15, no. 36 (2017): 7705–9. http://dx.doi.org/10.1039/c7ob01853c.

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Carlos Dias, Luiz. "Chiral Lewis Acid Catalyzed Ene-Reactions." Current Organic Chemistry 4, no. 3 (March 1, 2000): 305–42. http://dx.doi.org/10.2174/1385272003376274.

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Ogawa, Chikako, and Shu Kobayashi. "Chiral Lewis Acid Catalysis in Water." Current Organic Synthesis 8, no. 3 (June 1, 2011): 345–55. http://dx.doi.org/10.2174/157017911795529119.

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ISHIHARA, K., and H. YAMAMOTO. "ChemInform Abstract: Chiral Lewis Acid Catalysts." ChemInform 27, no. 36 (August 5, 2010): no. http://dx.doi.org/10.1002/chin.199636262.

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Rossi, Sergio, Tiziana Benincori, Laura Maria Raimondi, and Maurizio Benaglia. "3,3′-Bithiophene-Based Chiral Bisphosphine Oxides as Organocatalysts in Silicon-Derived Lewis Acid Mediated Reactions." Synlett 31, no. 06 (January 7, 2020): 535–46. http://dx.doi.org/10.1055/s-0039-1690777.

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This account summarizes the development of new biheteroaromatic chiral bisphosphine oxides. 3,3′-Bithiophene-based phosphine oxides (BITIOPOs) have been successfully used as organocatalysts to promote Lewis base catalyzed, Lewis acid mediated stereoselective transformations. These highly electron-rich compounds, in combination with trichorosilyl derivatives (allyltrichlorosilane and silicon tetrachloride), generate hypervalent silicon species that act as chiral Lewis acids in highly diastereo- and enantioselective organic reactions. Several relevant examples related to these applications are discussed in detail.1 Introduction2 The BITIOPO Family3 Enantioselective Opening of Epoxides4 Enantioselective Allylation of Aldehydes5 Stereoselective Direct (Double) Aldol-Type Reaction with Ketones6 Stereoselective Direct Aldol-Type Reaction with Ester Derivatives7 Conclusions
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Kobayashi, Shū. "Asymmetric catalysis in aqueous media." Pure and Applied Chemistry 79, no. 2 (January 1, 2007): 235–45. http://dx.doi.org/10.1351/pac200779020235.

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Lewis acid catalysis has attracted much attention in organic synthesis because of unique reactivity and selectivity attained under mild conditions. Although various kinds of Lewis acids have been developed and applied in industry, these Lewis acids must be generally used under strictly anhydrous conditions. The presence of even a small amount of water handles the reactions owing to preferential reactions of the Lewis acids with water rather than the substrates. In contrast, rare earth and other metal complexes have been found to be water-compatible. Several catalytic asymmetric reactions in aqueous media, including hydroxymethylation of silicon enolates with an aqueous solution of formaldehyde in the presence of Sc(OTf)3-chiral bipyridine ligand or Bi(OTf)3-chiral bipyridine ligand, Sc- or Bi-catalyzed asymmetric meso-epoxide ring-opening reactions with amines, and asymmetric Mannich-type reactions of silicon enolates with N-acylhydrazones in the presence of a chiral Zn catalyst have been developed. Water plays key roles in these asymmetric reactions.
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HAYASHI, Yujiro, and Koichi NARASAKA. "Chiral lewis acid in catalytic asymmetric reactions." Journal of Synthetic Organic Chemistry, Japan 48, no. 4 (1990): 280–91. http://dx.doi.org/10.5059/yukigoseikyokaishi.48.280.

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McKay, M. Kevin, and James R. Green. "Asymmetric synthesis based on chiral (arene)tricarbonylchromium acetal complexes. Addition reactions to the ortho-formyl complex." Canadian Journal of Chemistry 78, no. 12 (December 1, 2000): 1629–36. http://dx.doi.org/10.1139/v00-150.

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The addition reactions of organolithium and Grignard reagents to chiral, enantiomerically pure ortho-formyl (arene)tricarbonylchromium acetal complex (2) have been studied. The diastereoselectivity of the addition process is fair in the absence of an additional Lewis acid, and good in the presence of Ti(OiPr)4. The nature of the newly formed chiral centre, and studies on the possible nature of the nucleophilic species suggest that the Lewis acid acts through monodentate coordination to the aldehyde carbonyl, and thereby alters the carbonyl rotamer population more heavily in favour of the s-trans conformation. Nucleophilic attack then occurs on the face anti- to that bearing the Cr(CO)3 unit.Key words: (arene)tricarbonylchromium complexes, asymmetric synthesis, carbonyl additions, Lewis acids.
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Dissertations / Theses on the topic "Chiral Lewis acid"

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Knol, Jochem. "Chiral Lewis acid catalyzed Diels-Alder reactions." [S.l. : [Groningen : s.n.] ; University of Groningen] [Host], 2008. http://irs.ub.rug.nl/ppn/.

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Cao, Min. "Enantioselective Transformations Promoted by Cooperative Functions of an Achiral Lewis Acid and a Chiral Lewis Acid:." Thesis, Boston College, 2021. http://hdl.handle.net/2345/bc-ir:109203.

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Thesis advisor: Masayuki Wasa
Thesis advisor: Amir H. Hoveyda
This dissertation describes the development of cooperative catalyst systems that contain an achiral Lewis acid and a chiral Lewis acid that may have overlapping functions but play their independent roles to promote enantioselective C–C bond formations. Chapter 1 provides a summary of recent advances made in the field of enantioselective cooperative catalysis that served as intellectual foundations for this dissertation research. As it will be discussed in the first chapter, key limitations of cooperative catalysis are: (1) undesirable catalyst deactivation which occurs due to acid/base complexation, (2) requirement for base sensitive pronucleophiles and acid sensitive electrophiles, and (3) poor reaction efficiency. In an effort to overcome these fundamental limitations, we have developed “frustrated” Lewis pair (FLP)-based catalyst systems that consist of potent and sterically encumbered Lewis acids used in pair with bulky N-containing Lewis bases. To demonstrate the potential of the novel FLP catalyst system, we describe our work involving the enantioselective Conia-ene-type cyclization (Chapter 2). In the subsequent chapter (Chapter 3), we discuss the application of the FLP catalysts for enantioselective β-amino C–H functionalization reactions
Thesis (PhD) — Boston College, 2021
Submitted to: Boston College. Graduate School of Arts and Sciences
Discipline: Chemistry
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Mahal, R. S. "Preparation and use of chiral borane lewis acids." Thesis, University of Salford, 1988. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.381853.

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Clapham, Gary. "New Lewis acid promoted Diels-Alder reaction and transition catalysed hydrocarbons." Thesis, University of Exeter, 1998. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.284618.

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Mellberg, Annika. "Chiral Carbocations as Lewis Acid Catalysts in Diels-Alder Reactions." Thesis, KTH, Skolan för kemivetenskap (CHE), 2012. http://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-156209.

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Lewis acids can be used as catalysts in different reactions, but the term Lewis acid catalysts often refers to metal salts. Metal complexes have been widely used for asymmetric catalysis. Asymmetric synthesis can however be performed in a metal-free way by using organocatalysis. New Lewis acid catalysts that are more effective, enantioselective and environmental friendly is of interest. This new type of Lewis acid catalysts could for example be of carbocation based character. The aim of this project was to synthesize chiral carbocations with different degree of sterical hindrance and investigate their catalytic ability in Diels-Alder reactions. It was presumed that the Diels-Alder reactions were going to be performed in an asymmetric way since the carbocation catalysts were achiral. Two chiral carbocations were synthesized successfully. The first synthesized carbocation, the less sterical hindered compound 8, was formed as a racemic mixture. The second carbocation, compound 16, could be formed as an enatiomeric pure compound. Both carbocations showed catalytic ability in Diels-Alder reactions and compound 8 was comparable with some common Lewis acid catalysts. In general, when using compound 8 as catalyst, higher catalyst amount gave higher conversions. Higher concentrations also gave higher conversions, but up to a certain level. No trend between polarity of different solvents and conversions could be seen. However, an increased temperature leads to faster reactions. The more rigid and sterical hindered compound 16 catalyzed the reactions slower than compound 8. The longer reaction time may indicate that the reaction occurs with higher selectivity, but no method to measure the ee of the product was found. An attempt to synthesize a third even more sterical hindered chiral carbocation, compound 19, resulted in a product contaminated by impurities that showed a catalytic ability lower than compound 8 and compound 16 in Diels-Alder reactions. The synthesis and the use of carbocations as Lewis acid catalysts in Diels-Alder reactions seem promising as a new type of catalysts even though there are questions that are still unanswered, e.g. counter ions effects, possible side reactions, selectivity etc.
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Risberg, Erik. "Lewis acid Mediated Aza-Diels-Alder Reactions and Asymmetric Alkylations of 2H-azirines." Doctoral thesis, KTH, Chemistry, 2004. http://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-3822.

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This thesis describes the use of 2H-azirines, three-membered unsaturatednitrogen-containing heterocycles, as reactive intermediates ina number of Lewis acid promoted alkylations and Diels-Alderreactions providing synthetically useful aziridines.

In order to carry out this investigation a new generalprocedure for the ring closure of vinyl azides, forming theresultant 3-substituted-2H-azirines, was developed applying low boiling solventsin closed reaction vessels at elevated temperatures.

The addition of organolithium reagents in the presence ofcommercially available chiral ligands, to the 3-(2-naphthyl)-2H-azirine was studied, which gave the correspondingaziridines.

Several Lewis acids were shown to catalyze the normalelectron-demand Diels-Alder reaction between 3-alkyl-,3-aromatic-, and 3-ester-substituted 2H-azirines and various dienes. These reactions gave theexpected cycloadducts in moderate yields.

Using a chiral auxiliary high diastereoselectivity wasobtained in the addition of alkyl radicals to a8-phenylmenthyl-substituted 2H-azirine-3-carboxylate. The alkyl radicals weregenerated from the corresponding trialkyl borane and molecularoxygen. Hydroborations and transmetallations were used toprepare these trialkylboranes. Catalytic amounts of CuClincreased the diastereoselectivity in the radical additionreactions.

Attempts were made to explain how the coordination of aLewis acid to the azirine nitrogen atom affects thereactivity/stability of the azirine. DFT calculations and NMRexperiments involving Lewis acid-azirine complexes wereperformed.

Keywords:Enantioselective, diastereoselective, vinylazide, 2H-azirines, aziridines, Lewis acid, chiral ligand,chiral auxiliary, organolithiums, Diels-Alder reaction, alkylradicals, triethylborane.

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Lundgren, Stina. "Efficient Synthesis and Analysis of Chiral Cyanohydrins." Doctoral thesis, Stockholm : Kungliga Tekniska högskolan (KTH), 2007. http://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-4315.

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Risberg, Erik. "Lewis Acid Mediated Alkylation and Diels-Alder Reactions of 2H-Azirines." Licentiate thesis, KTH, Chemistry, 2002. http://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-1489.

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This thesis describes the use of 2H-azirines as reactivesubstrates in Lewis acid catalysed nucleophilic additions andin the Diels-Alder reaction.A number of carbon nucleophiles have been added to aseries of 2H-azirines in the presence and absence ofBF3·Et2O. 3-(2-Naphthyl)-2H-azirine has been used as amodel substrate in the enantioselective addition oforganolithium reagents to an 2H-azirine.A selection of Lewis acids has been screened for theirpossible use in the normal electron demand Diels-Alder reactionbetween 3-alkyl-, 3-aryl-, and 3- carboxyl-2H-azirines and avariety of dienes. Lewis acid activation was found to shortenreaction times and facilitate lower reaction temperatures.These cycloadditions proceeded with endo selectivity providinga single diastereoisomeric product.DFT calculations of Lewis acid activated 2H-azirineshave been carried out.

Keywords:2H-azirines, Lewis acid activation, chiralligands, organolithium reagents, Diels-Alder reactions,DFT-calculations

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Wingstrand, Erica. "New Methods for Chiral Cyanohydrin Synthesis." Doctoral thesis, KTH, Kemi, 2009. http://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-10205.

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This thesis deals with method development in asymmetric catalysis and specifically syntheses of enantioenriched O-functionalized cyanohydrins. The first part describes the development of a method for the synthesis of O‑alkoxycarbonylated and O-acylated cyanohydrins. Ethyl cyanoformate and acyl cyanides were added to aldehydes in a reaction catalyzed by a chiral dimeric Ti-salen complex together with a tertiary amine. High yields and enantioselectivities were in most cases obtained. Mechanistic studies were performed and a reaction mechanism was proposed. ­ The second part describes a method in which the undesired minor enantiomer in a Lewis acid–Lewis base-catalyzed acylcyanation is continuously recycled into prochiral starting material. Close to enantiopure O‑acylated cyanohydrins were obtained in high yields. The third part deals with asymmetric acylcyanations of ketones. Acetyl cyanide was found to add to α‑ketoesters in a reaction catalyzed by a chiral Lewis base. Yields up to 77% and 82% ee were obtained. The final part describes an enzymatic method for high-throughput analysis of O‑acylated cyanohydrins. The enantiomeric excess and conversion were determined for products obtained from a number of aromatic and aliphatic aldehydes.
QC 20100818
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Chang, Yejin. "Enantioselective Transformations of α- and β-Amino C-H Bonds Promoted by Cooperative Actions of Achiral and Chiral Lewis Acid Catalysts:." Thesis, Boston College, 2021. http://hdl.handle.net/2345/bc-ir:109179.

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Thesis advisor: Masayuki Wasa
Thesis advisor: Amir H. Hoveyda
This dissertation describes the development of cooperative catalyst systems for the regio- and enantio-selective α- and β-amino C-H functionalization of N-alkylamines, inspired by the concepts of frustrated Lewis pairs (FLPs). Prior to this dissertation research, the development of effective and broadly applicable catalytic protocol to transform amino C-H bonds with high enantioselectivity remained as a formidable problem. In Chapter 1, the recent advances in the field of amino C-H functionalization through hydride transfer process that served as intellectual foundations for this dissertation research is presented. As highlighted in the first chapter, key challenges of amino C-H functionalization are: (1) unreactive nature of α, β- and/or γ-amino C-H bonds, (2) requirement for the use of precious metal-based catalysts and external oxidants under acidic/basic and harsh conditions, (3) use of directing groups for regioselectivity, and (4) poor functional group tolerance. Inspired by the unique capability of FLPs to activate otherwise unreactive molecules while disfavoring undesirable acid-base complexation, we have developed a protocol for enantioselective α-amino C-H functionalization of N-alkylamines, where chiral and achiral Lewis acid catalysts work cooperatively (Chapter 2). The application of the cooperative catalyst system comprising of B(C6F5)3, a chiral Lewis acid, and a Brønsted base to the enantioselective β-amino C-H functionalization is described in Chapter 3
Thesis (PhD) — Boston College, 2021
Submitted to: Boston College. Graduate School of Arts and Sciences
Discipline: Chemistry
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Books on the topic "Chiral Lewis acid"

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H. R. R. De Silva. Lewis-acid catalysed synthesis of chiral 1,2-diols. Manchester: UMIST, 1995.

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Mikami, Koichi, ed. Chiral Lewis Acids. Cham: Springer International Publishing, 2018. http://dx.doi.org/10.1007/978-3-319-70806-5.

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Mlynarski, Jacek, ed. Chiral Lewis Acids in Organic Synthesis. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2017. http://dx.doi.org/10.1002/9783527802142.

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Mahal, Ravinderjit Singh. Preparation and use of chiral borane Lewis acids. Salford: University of Salford, 1988.

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Chiral Lewis Acids. Springer, 2019.

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Mikami, Koichi. Chiral Lewis Acids. Springer, 2018.

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Chiral Lewis Acids in Organic Synthesis. Wiley & Sons, Limited, John, 2017.

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Mlynarski, Jacek. Chiral Lewis Acids in Organic Synthesis. Wiley & Sons, Incorporated, John, 2017.

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Mlynarski, Jacek. Chiral Lewis Acids in Organic Synthesis. Wiley & Sons, Incorporated, John, 2017.

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Book chapters on the topic "Chiral Lewis acid"

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Yamamoto, Hisashi, Keiji Maruoka, and Kyoji Furuta. "Chiral Lewis Acid Catalysts Organoaluminum and Boron Reagent." In Selectivities in Lewis Acid Promoted Reactions, 281–94. Dordrecht: Springer Netherlands, 1989. http://dx.doi.org/10.1007/978-94-009-2464-2_15.

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Paterson, Ian. "Aldol Condensations of Ketones Using Chiral Boron Reagents." In Selectivities in Lewis Acid Promoted Reactions, 311. Dordrecht: Springer Netherlands, 1989. http://dx.doi.org/10.1007/978-94-009-2464-2_24.

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Brill, Marcel, and Steven P. Nolan. "Chiral Carbophilic Gold Lewis Acid Complexes in Enantioselective Catalysis." In Topics in Organometallic Chemistry, 51–90. Cham: Springer International Publishing, 2015. http://dx.doi.org/10.1007/3418_2015_142.

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Feng, Xiaoming, Zhen Wang, and Xiaohua Liu. "Chiral Lewis Acid Rare-Earth Metal Complexes in Enantioselective Catalysis." In Topics in Organometallic Chemistry, 147–91. Cham: Springer International Publishing, 2017. http://dx.doi.org/10.1007/3418_2017_1.

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Shibasaki, Masakatsu, and Naoya Kumagai. "Chiral Bimetallic Lewis Acids." In Topics in Organometallic Chemistry, 27–50. Cham: Springer International Publishing, 2015. http://dx.doi.org/10.1007/3418_2015_153.

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Wang, Jun, and Xiaoming Feng. "Titanium-Based Chiral Lewis Acids." In Chiral Lewis Acids in Organic Synthesis, 27–57. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2017. http://dx.doi.org/10.1002/9783527802142.ch2.

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Ollevier, Thierry. "Iron-based Chiral Lewis Acids." In Chiral Lewis Acids in Organic Synthesis, 59–101. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2017. http://dx.doi.org/10.1002/9783527802142.ch3.

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Karthikeyan Iyanar and Mukund P. Sibi. "Copper-based Chiral Lewis Acids." In Chiral Lewis Acids in Organic Synthesis, 103–35. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2017. http://dx.doi.org/10.1002/9783527802142.ch4.

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Baś, Sebastian, Marcin Szewczyk, and Jacek Mlynarski. "Zinc-based Chiral Lewis Acids." In Chiral Lewis Acids in Organic Synthesis, 137–81. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2017. http://dx.doi.org/10.1002/9783527802142.ch5.

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Aspinall, Helen C. "Chiral Rare Earth Lewis Acids." In Chiral Lewis Acids in Organic Synthesis, 261–98. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2017. http://dx.doi.org/10.1002/9783527802142.ch8.

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