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Relevant bibliographies by topics / Ketenes. Esters. Acetals

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Academic literature on the topic 'Ketenes. Esters. Acetals'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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Journal articles on the topic "Ketenes. Esters. Acetals"

1

Mulzer, Johann, Dirk Trauner та Jan W. Bats. "Stereoselective Insertion of Ketenes into O,O-Acetals: Synthesis ofβ-Alkoxy Esters and 1,4-Dioxepan-5-ones". Angewandte Chemie International Edition in English 35, № 17 (1996): 1970–72. http://dx.doi.org/10.1002/anie.199619701.

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Charlton, M. Anne, and James R. Green. "Formation of quaternary centres via iron allyl cations. Rapid entry into spirocyclic ring systems." Canadian Journal of Chemistry 75, no. 7 (1997): 965–74. http://dx.doi.org/10.1139/v97-116.

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Ester-substituted allyltetracarbonyliron cations react with cycloalkylidene-type silyl enol ethers, silyl ketene acetals, and β-keto-esters to give 1,6-dicarbonyl compounds containing a newly formed quaternary centre. Selected condensation products are converted by enolate chemistry into spirocyclic [4.4], [4.5], and [4.6] systems. Acyloin and other reductive cyclization reactions are employed to convert the condensation products into spirocyclic [4.5], [5.5], and [5.6] systems. Keywords: allyliron complexes, umpolung synthesis, 1,6-dicarbonyls, spirocycle synthesis.

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3

Lampland, Nicole L., Aradhana Pindwal, Steven R. Neal, Shealyn Schlauderaff, Arkady Ellern та Aaron D. Sadow. "Magnesium-catalyzed hydrosilylation of α,β-unsaturated esters". Chemical Science 6, № 12 (2015): 6901–7. http://dx.doi.org/10.1039/c5sc02435h.

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Jackson, Alexander W., Srinivasa Reddy Mothe, Lohitha Rao Chennamaneni, Alexander van Herk, and Praveen Thoniyot. "Unraveling the History and Revisiting the Synthesis of Degradable Polystyrene Analogues via Radical Ring-Opening Copolymerization with Cyclic Ketene Acetals." Materials 13, no. 10 (2020): 2325. http://dx.doi.org/10.3390/ma13102325.

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Degradable analogues of polystyrene are synthesized via radical ring-opening (co)polymerization (rROP) between styrene and two cyclic ketene acetals, namely 2-methylene-1,3-dioxepane (MDO) and 5,6-benzo-2-methylene-1,3-dioxepane (BMDO). This approach periodically inserts ester bonds throughout the main chain of polystyrene, imparting a degradation pathway via ester hydrolysis. We discuss the historical record of this approach, with careful attention paid to the conflicting findings previously reported. We have found a common 1H NMR characterization error, repeated throughout the existing body

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5

Collins, David J., and Ian T. Crosby. "Enolic Ortho Esters. VIII Synthesis of (2S,3S)-2,3-Bis(methoxymethyl)-1,4,6-trioxaspiro[4.5]dec-7-ene." Australian Journal of Chemistry 51, no. 11 (1998): 1025. http://dx.doi.org/10.1071/c98085.

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Enolic ortho ester (2S,3S)-2,3-bis(methoxymethyl)-1,4,6-trioxaspiro[4.5]dec-7-ene (10b) was synthesized in 65% yield by cycloadditon of acrolein with the ketene acetal (4S,5S)-4,5-bis(methoxymethyl)-2-methylidene-1,3-dioxolan (7), derived by potassium t-butoxide treatment of (4S,5S)-4,5-bis(methoxy- methyl)-1,3-dioxolan (4). Lewis acid catalysed reaction (TiCl4, CH2Cl2, –78°) of the enolic ortho ester (10b) with the ketene silyl acetal 3-phenylmethyl-2-trimethylsilyloxy-4,5-dihydrofuran (15) afforded the formyl keto ester 3-[4′,5′-bis(methoxymethyl)-2′-(4′′-oxobutyl)-1′,3′-dioxolan-2′-yl]-3-ph

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6

Engesser, Tobias, and Reinhard Brückner. "Stereoselective Aldol Additions of Glycolic Acid and Its Derivatives." Synthesis 51, no. 08 (2019): 1715–45. http://dx.doi.org/10.1055/s-0037-1611721.

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This review gives a comprehensive overview of aldol additions of glycolic acid derivatives to achiral aldehydes and acetals affording α,β-dihydroxycarboxylic acids or derivatives thereof. The focus is on simple diastereoselectivity. A selection of related aldol additions is also presented: aldol additions of glycolic acid derivatives to ketones with two different substituents and aldol additions of α-substituted glycolic acid derivatives.1 Introduction1.1 Organization of this Review1.2 Outside the Scope of this Review: Aldol Additions Giving α,β-Dihydroxyaldehydes and α,β-Dihydroxyketones Dias

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Suginome, Michinori. "Aminoboranes as new iminium ion generators in amination reactions." Pure and Applied Chemistry 78, no. 7 (2006): 1377–87. http://dx.doi.org/10.1351/pac200678071377.

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The utilization of aminoborane derivatives in amination reactions such as Strecker-type aminative cyanation, Mannich-type reaction, and reductive amination is described. Bis(dialkylamino)cyanoboranes and bis(dialkylamino)boron enolates underwent the concurrent transfer of the amino group and either the cyano or the enoxy group from the boron to carbonyl carbon atom in their reaction with aldehydes, leading to the formation of α-amino nitriles and β-amino ketones, respectively. Bis(dialkylamino)borane derivatives that lack the additional nucleophilic groups on the boron atoms were found to serv

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8

Jiang, Xingyu, and John F. Hartwig. "Iridium-Catalyzed Enantioselective Allylic Substitution of Aliphatic Esters with Silyl Ketene Acetals as the Ester Enolates." Angewandte Chemie International Edition 56, no. 30 (2017): 8887–91. http://dx.doi.org/10.1002/anie.201704354.

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9

Jiang, Xingyu, and John F. Hartwig. "Iridium-Catalyzed Enantioselective Allylic Substitution of Aliphatic Esters with Silyl Ketene Acetals as the Ester Enolates." Angewandte Chemie 129, no. 30 (2017): 9013–17. http://dx.doi.org/10.1002/ange.201704354.

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10

Collins, DJ, GLP Choo та H. Obrist. "Preparation of β-Keto Ester Acetals by Reaction of Ortho Esters With Ketene Silyl Acetals in the Presence of Titanium Tetrachloride". Australian Journal of Chemistry 43, № 3 (1990): 617. http://dx.doi.org/10.1071/ch9900617.

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Reaction of 2-ethoxy-2-methyl-1,3-dioxolan (1c) with 1-methoxy-1-trimethylsilyloxyethene (4a) in dichloromethane in the presence of titanium tetrachloride gave 62% of methyl 2-(2′-methyl-1′,3′-dioxolan-2′-yl)acetate (5a). Similarly, reaction of (1c) with l-methoxy-1-trimethylsilyloxyprop-1-ene (4b) afforded 73% of methyl 2-(2′-methyl-1′,3′-dioxolan-2′-yl) propanoate (5b).

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Dissertations / Theses on the topic "Ketenes. Esters. Acetals"

1

Ray, Colin Andrew. "Development of a recyclable acetic ester enolate equivalent." Thesis, University of Salford, 2001. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.365994.

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Ramiandrasoa, Guy. "Etude de l'accès sélectif aux esters 2,3-difonctionnels." Rouen, 1993. http://www.theses.fr/1993ROUES017.

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Plusieurs voies d'accès aux esters 2,3-difonctionnels ont été évaluées dans les séries dihydroxy- et aminohydroxyesters en raison de l'importance des produits naturels correspondants ou de leurs homologues synthétiques. Les précurseurs de ces synthèses sont les α et β cétoesters fonctionnels et leurs formes protégées ainsi que les dérivés silylés des dialkoxyacétates d'alkyle, acétals de cétène silylés fonctionnels qui représentent les équivalents synthétiques des synthons C2 oxoester « CO-COOR ». L'étude structurale des composés préparés est axée sur la RMN 1H et 13C ainsi que sur les caracté

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3

Hiouni, Abdelaziz. "Première synthèse des α-lithioacétals de cétène : condensation avec les dérivés carbonylés". Rouen, 1996. http://www.theses.fr/1996ROUES074.

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Pour la première fois des alpha-lithioacétals de cétène ont été obtenus. Ils ont été préparés par échange brome-lithium à partir de bromoacétals de cétène. La condensation de ces réactifs à fonction ester masquée conduit soit à des esters α, β-éthyléniques (hydrolyse acide), soit à des β-hydroxyesters (hydrolyse basique). De plus la protonation de l'intermédiaire de condensation lithié par le bromure de tertio-butyle conduit a des β-hydroxyacétals de cétène, non décrits dans la littérature. Dans certains cas la supériorité de ces lithioacétals de cétène par rapport aux réactifs classiques (Ref

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4

Aspin, Samuel. "Arylation migratoire C(sp3)-H d'énolates d'esters." Thesis, Lyon 1, 2013. http://www.theses.fr/2013LYO10298.

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La fonctionnalisation C(sp3)-H catalysée par des métaux de transitions, ouvre de nombreuses perspectives en synthèse organique, permettant des voies d'accès plus économes en atomes, et en étapes à des molécules à forte valeur ajoutée. Dans cette optique, une méthode efficace permettant l'arylation des liaisons C(sp3)-H en position α d'un groupement attracteur, plus communément appelée α -arylation a récemment fait l'objet d'une attention toute particulière de la part de la communauté scientifique. Le travail détaillé dans ce manuscrit décrit les dernières avancées de cette méthodologie, ainsi

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Book chapters on the topic "Ketenes. Esters. Acetals"

1

Ziegler, T. "Synthesis from Ketenes, Ketene Acetals, or Ynamines." In Three Carbon-Heteroatom Bonds: Esters and Lactones; Peroxy Acids and R(CO)OX Compounds; R(CO)X, X=S, Se, Te. Georg Thieme Verlag KG, 2005. http://dx.doi.org/10.1055/sos-sd-021-00058.

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2

Kostikov, R. R. "Synthesis of Esters by Mukaiyama-Type Condensation of Acetals." In Three Carbon-Heteroatom Bonds: Ketenes and Derivatives. Georg Thieme Verlag KG, 2006. http://dx.doi.org/10.1055/sos-sd-024-00150.

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3

Kantlehner, W. "Elimination of Alcohols or Amines from Amide ,-Acetals or Ester ,-Acetals." In Three Carbon-Heteroatom Bonds: Ketenes and Derivatives. Georg Thieme Verlag KG, 2006. http://dx.doi.org/10.1055/sos-sd-024-00427.

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4

Friesen, R. W. "γ,δ-Unsaturated Esters from Allylation of Ketene Silyl Acetals." In Compounds with Transition Metal-Carbon pi-Bonds and Compounds of Groups 10-8 (Ni, Pd, Pt, Co, Rh, Ir, Fe, Ru, Os). Georg Thieme Verlag KG, 2001. http://dx.doi.org/10.1055/sos-sd-001-00138.

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5

Trauner, D. "Mild Hydrolysis of Enol Ketene Acetals or Enol Ortho Esters." In X-Ene-X (X=F, Cl, Br, I, O, S, Se, Te, N, P), Ene-Hal, and Ene-O Compounds. Georg Thieme Verlag KG, 2008. http://dx.doi.org/10.1055/sos-sd-032-00575.

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6

Iesce, M. R., and M. DellaGreca. "Acid-Catalyzed Reaction of Peroxyketals with Ketene Silyl Acetals." In Peroxides, Inorganic Esters (RO-X, X=Hal, S, Se, Te, N). Georg Thieme Verlag KG, 2009. http://dx.doi.org/10.1055/sos-sd-038-00311.

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7

Friesen, R. W. "α,β-Unsaturated Esters from Dehydrogenation of Saturated Esters via Their Ketene Silyl Acetals." In Compounds with Transition Metal-Carbon pi-Bonds and Compounds of Groups 10-8 (Ni, Pd, Pt, Co, Rh, Ir, Fe, Ru, Os). Georg Thieme Verlag KG, 2001. http://dx.doi.org/10.1055/sos-sd-001-00130.

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8

Taber, Douglass F. "The Williams Synthesis of (-)-4-Hydroxydictyolactone." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0083.

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(-)-4-Hydroxydictyolactone 3, representative of the cyclononene xenicanes isolated from the Dictyotacae algae, readily isomerizes thermally to the more stable ( Z )- 6,7-isomer. Attempts to directly form this strained ring system appeared to be fraught with difficulty. David R. Williams of Indiana University envisoned (J. Am. Chem. Soc. 2009, 131, 9038) that use of Suzuki coupling might ameliorate some of the strain, since at the point of commitment to bond formation, the Pd center would be included in the forming ring. This analysis led specifically to the trans ether 1, as cyclization of the trans ether appeared likely to be more facile than would cyclization of the alternative cis diastereomer. The first challenge was the assembly of the array the four contiguous alkylated stereogenic centers of 1. To this end, the Z secondary ester 7 was prepared from the acetonide 4 , available from mannitol, and ( R )-(+)-citronellic acid, prepared by oxidation of the commercial aldehyde. Addition of 7 to LDA led to decomposition, but inverse addition of LDA to a mixture of the ester, TMSCl, and Et3 N smoothly delivered the ketene silyl acetal. On warming, Ireland-Claisen rearrangement of the ketene silyl acetal led to the acid 8 with remarkable diastereocontrol. The last alkylated stereogenic center of 1 was installed by reductive cyclization of the formate ester 9. Again, the cyclization proceeded with remarkable diastererocontrol. Although the intramolecular reaction of in situ prepared allyl metals is well precedented, the addition to a formate ester had not previously been reported. Although 11 appears to be ready for the long-awaited Suzuki coupling, in fact the TIPS protecting group substantially slowed hydroboration. The free alcohol/methyl acetal was the best substrate for hydroboration, but the free alcohol entered into other side reactions. After extensive experimentation, a happy medium was found with the methyl acetal/TBS ether 1. Selenylation of the lactone 12 followed by oxidative elimination of the selenide delivered the expected Z alkene. Removal of the silyl protecting group had to precede introduction of the second alkene, as the product 3 deteriorated rapidly on exposure to the alkaline conditions of TBAF cleavage.

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9

Phillips, A. J., and C. E. Love. "Rearrangement of Ketene Acetals Derived from Ortho Esters (The Johnson Protocol)." In Three Carbon-Heteroatom Bonds: Acid Halides; Carboxylic Acids and Acid Salts. Georg Thieme Verlag KG, 2007. http://dx.doi.org/10.1055/sos-sd-020-00764.

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10

Smith, M. B. "By Lewis Acid Catalyzed Addition of Silyl Ketene Acetals to Nitroalkenes." In Three Carbon-Heteroatom Bonds: Esters and Lactones; Peroxy Acids and R(CO)OX Compounds; R(CO)X, X=S, Se, Te. Georg Thieme Verlag KG, 2005. http://dx.doi.org/10.1055/sos-sd-021-00619.

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