Relevant bibliographies by topics / Enantiodivergent

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Academic literature on the topic 'Enantiodivergent'

Author: Grafiati
Published: 4 June 2021
Last updated: 15 February 2022

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Journal articles on the topic "Enantiodivergent"

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Westermann, Bernhard, Muhammad Ayaz, and Sander S van Berkel. "Enantiodivergent Organocascade Reactions." Angewandte Chemie International Edition 49, no. 5 (December 22, 2009): 846–49. http://dx.doi.org/10.1002/anie.200904638.

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Sohtome, Yoshihiro, and Kazuo Nagasawa. "Sequential stereodivergent organocatalysis and programmed organocascades." Org. Biomol. Chem. 12, no. 11 (2014): 1681–85. http://dx.doi.org/10.1039/c3ob42310g.

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Geiger, Yannick, Thierry Achard, Aline Maisse-François, and Stéphane Bellemin-Laponnaz. "Hyperpositive non-linear effects: enantiodivergence and modelling." Chemical Science 11, no. 46 (2020): 12453–63. http://dx.doi.org/10.1039/d0sc04724d.

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Cao, Weidi, Xiaoming Feng, and Xiaohua Liu. "Reversal of enantioselectivity in chiral metal complex-catalyzed asymmetric reactions." Organic & Biomolecular Chemistry 17, no. 27 (2019): 6538–50. http://dx.doi.org/10.1039/c9ob01027k.

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Sivamuthuraman, Koilpitchai, and Venkitasamy Kesavan. "Catalytic enantioselective Michael addition of 2-substituted benzofuran-3-ones to 2-enoyl pyridines." Organic & Biomolecular Chemistry 17, no. 30 (2019): 7166–71. http://dx.doi.org/10.1039/c9ob01069f.

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Oczipka, P., D. Müller, W. Leitner, and G. Franciò. "Enantiodivergent asymmetric catalysis with the tropos BIPHEP ligand and a proline derivative as chiral selector." Chemical Science 7, no. 1 (2016): 678–83. http://dx.doi.org/10.1039/c5sc03465e.

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Chen, Chien-Tien, Cheng-Che Tsai, Pei-Kang Tsou, Gou-Tao Huang, and Chin-Hui Yu. "Enantiodivergent Steglich rearrangement of O-carboxylazlactones catalyzed by a chirality switchable helicene containing a 4-aminopyridine unit." Chemical Science 8, no. 1 (2017): 524–29. http://dx.doi.org/10.1039/c6sc02646j.

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Nagamoto, Midori, Daisuke Yamauchi, and Takahiro Nishimura. "Iridium-catalyzed asymmetric [3+2] annulation of aromatic ketimines with alkynes via C–H activation: unexpected inversion of the enantioselectivity induced by protic acids." Chemical Communications 52, no. 34 (2016): 5876–79. http://dx.doi.org/10.1039/c6cc01398h.

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Xie, Shaolei, Zhi-Juan He, Ling-Hui Zhang, Bo-Lun Huang, Xiao-Wei Chen, Zong-Song Zhan, and Fu-Min Zhang. "The organocatalytic enantiodivergent fluorination of β-ketodiaryl-phosphine oxides for the construction of carbon-fluorine quaternary stereocenters." Chemical Communications 57, no. 16 (2021): 2069–72. http://dx.doi.org/10.1039/d0cc07770d.

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We developed, for the first time, the cinchona-alkaloid-catalyzed enantiodivergent α-fluorination of β-keto diarylphosphine oxides, which resulted in two enantiomers bearing fluorine-containing quaternary stereocenters.
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Pazos, Gonzalo, Manuel Pérez, Zoila Gándara, Generosa Gómez, and Yagamare Fall. "Enantiodivergent synthesis of (+)- and (−)-isolaurepan." Tetrahedron 68, no. 44 (November 2012): 8994–9003. http://dx.doi.org/10.1016/j.tet.2012.08.094.

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Dissertations / Theses on the topic "Enantiodivergent"

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Pérez, Diez Laura. "Síntesi Enantiodivergent de la (+)- i (-)-isolineatina." Doctoral thesis, Universitat Autònoma de Barcelona, 2014. http://hdl.handle.net/10803/133321.

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La (+)-Lineatina es el component principal de la feromòna d’agregació segregada per la femella de l’escarabat de l’ambrosia Trypodendron lineatum, que es una plaga que afecta als boscos de coníferes d’Europa i Nord La Isolineatina és un isòmer constitucional de la lineatina que s’ha descrit com un coproducte en algunes de les diferents aproximacions sintètiques cap a la lineatina. Fins ara, només el treball publicat per Askani i Keller té com a objectiu principal la síntesis de la isolineatina en forma racèmica. Aquesta es porta a a terme a partir de l’anhídrid maleic en un aseqüència d’11 etapes i amb un rendiment global al voltant de l’1%. En el present treball s’ha assolit la primera síntesi enantioselectiva de la (+)- i la (-)- isolineatina utilitzant com a pas clau de formació de l’anell ciclobutànic funcionalitzat a partir de la reacció de fotocicloaddició [2+2] de la (S)-4-metil-5-pivaloximetil-2(5H)- furanona a 1,1-dietoxietilè. Per a realitzar aquesta etapa s’ha realitzat un estudi de l’efecte del dissolvent en la regioselectivitat i la diastereoselectivitat facial en la reacció de cicloaddició fotoquímica de 5-O-derivats de la (S)-4-metil-5-hidroximetil-2(5H)- furanona a 1,1-dietoxietilè. Els millors resultats pels nostres objectius sintètics s’aconsegueixen en utilitzar èter com a dissolvent. D’aquesta manera s’obtenen els fotocicloadductes anti cap-cua amb un 46% de rendiment i el sin cap-cua amb un 38% de rendiment. A partir dels fotocicloadductes s’han desenvolupat quatre rutes encaminades als productes objectiu. En la darrera, s’ha obtingut la (-)-isolineatina mitjançant la ruta sintètica que consta de 10 etapes amb un rendiment global del 7% i la (+)-isolineatina en 12 etapes i un rendiment global del 5 %.
(+)-Lineatin is the main component of the aggregation pheromone produced by the female ambrosia beetle Trypodendron lineatum , which is a damaging pest to coniferous forest in Europe and North America. Isolineatin a constitutional isomer of lineatin has often been described as a by-product in some of the lineatin syntheses. However, to date, only one publication, reported by Askani and Keller, describes the synthesis of racemic isolineatin through a sequence specifically devoted to this target starting from maleic anhydride in 11 steps and around 1% overall yield. In this thesis we report the first successful enantiodivergent synthesis of both enantiomers of isolineatin. The main step is the preparation of the chiral platform through the regioselective [2+2] photochemical cycloaddition reaction from the (S)-4- metil-5-pivaloximetil-2(5H)-furanone with 1,1-diethoxyethylene. In order to carry out this task, we have performed the study of the solvent effect in the stereochemical course of the photochemical cycloaddition of different 5-O-acyl substituted (S)-4-methyl-5- hidroximethyl-2(5H)-furanones with 1,1-diethoxyethylene. It has been found that when the reaction was performed in diethyl ether the process occurs with excellent regioselectivity giving the HT anti and syn isomers with 46% and 38% yield, respectively. From these photocycloadducts, four synthetic approaches to (-)- and (+)-isolineatin have been developed. Eventually, the last designed route led to (-)-isolineatin in 7% overall yield in 10 steps and to its dextrogir isomer in 5% overall yield in 12 steps.
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Biswas, Souvagya. "Asymmetric Catalysis of Carbon-Carbon Bond Forming Reactions: Use of a Sustainable Feedstock Ethylene." The Ohio State University, 2016. http://rave.ohiolink.edu/etdc/view?acc_num=osu1449830785.

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DUCLOS, OLIVIER. "Cycloheptanes polyfonctionnalises derives du d-glucose : synthese enantiodivergente des (+) et (-)-calystegine b#2." Paris 6, 1994. http://www.theses.fr/1994PA066357.

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Les calystegines sont des alcaloides nortropaniques polyhydroxyles qui ont ete recemment isoles de plantes parmi lesquelles calystegia sepium, et dont les structures se caracterisent par la presence d'une fonction hemiaminale situee en jonction de cycles. Ce travail a porte sur la synthese totale de la calystegine b#2 et nous a amene a developper une nouvelle methode d'acces a des cycloheptitols enantiomeriquement purs. Dans une premiere partie, nous avons envisage former le motif cycloheptanique de la calystegine b#2 au cours d'une cyclisation anionique (reaction de dieckmann ou d'hydroxyalkylation) effectuee sur un derive acyclique du d-glucose. Malheureusement, dans les deux cas etudies, l'introduction de tous les groupes fonctionnels requis a echoue et la validite de cette approche n'a donc pu etre etablie. Dans une deuxieme partie, nous decrivons la preparation de cycloheptanes polyfonctionnalises optiquement actifs a partir du d-glucose. L'etape cle est la formation du carbocycle, sous forme d'une cycloheptano-isoxazoline, par une reaction de cycloaddition 1,3-dipolaire diastereoselective effectuee sur un oxyde de nitrile ethylenique. Ensuite, une cycloheptano-isoxazoline derivee du d-glucose nous a servi de precurseur commun pour la synthese totale des (+) et (-)-calystegines b#2 et celle d'un analogue hydroxymethyle. Ces nortropanes ont ete obtenus, lors de l'ultime etape, par cyclisation intramoleculaire des 5-aminocycloheptanones polyhydroxylees correspondantes. Finalement, ces composes synthetiques ont fait l'objet d'une etude biologique comme mediateurs chimiques, inhibiteurs de glycosidases et anti-hiv1. Nos resultats ont permis de confirmer la structure de la calystegine b#2 et d'etablir que la molecule naturelle etait l'enantiomere dextrogyre de configuration absolue (1r,2s,3r,4s,5r)
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4

Goran, Benedeković. "Enantiodivergentna totalna sinteza odabranih stiril laktona i preliminarno ispitivanje njihove citotoksičnosti." Phd thesis, Univerzitet u Novom Sadu, Prirodno-matematički fakultet u Novom Sadu, 2012. http://dx.doi.org/10.2298/NS20121011BENEDEKOVIC.

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U radu je ostvarena enantiodivergentna totalna sinteza oba enantiomera goniofufurona, 7-epi-goniofufurona i krasalaktona C polazeći iz D-glukoze. Ključne faze u sintezi 7-epi-(+)-goniofufurona bile su stereoselektivna adicija fenilmagnezijum bromida na aldehidnu grupu pogodno zaštićene dialdoze, i stereospecifično formiranje furano-laktonskog prstena ciklokondenzacijom odabranog hemiacetalnog derivata sa Meldrum-ovom kiselinom. Sinteza (+)-goniofufurona i (+)-krasalaktona C zahtevala je inverziju konfiguracije na C-5u zajedničkom intermedijeru, koja je efikasno ostvarena u uslovima Mitsunobu-ove reakcije, ili alternativno oksidacijom benzilne hidroksilne grupe u prohiralni keton, uz naknadnu stereoselektivnu redukcijom sa borohidridom. Sličan pristup je zatim primenjen za sintezu neprirodnih (−)-enantiomera goniofufurona, 7-epi-goniofufurona i krasalaktona C, dva nova konformaciono ograničena analoga (+)- i (−)-goniofufurona (oksetani 36 i ent-36), kao i odgovarajućih 7-deoksigenovanih derivata (31 i ent-31). Takodje je razvijena i prva totalna sinteza prirodnog (+)-krasalaktona B (3) i alternativna sinteza (+)-krasalaktona C (4) polazeći iz D-glukoze. Selektivni pristup molekulima 3, odnosno 4 omogućen je promenom uslova za TBDPS deprotekciju u finalnom intermedijeru 53. Osnovna karakteristika pomenutih pristupa je njihova generalnost i fleksibilnost. Na taj način je omogućena sinteza serije analoga i derivata (+)-goniofufurona, ili 7-epi-goniofufurona, uključujući i do sada nepoznate 7-epi-(+)-krasalaktone B (6) i C (7), 5,7-di-O-cinamoil derivate 8 i 9, 5,7-di-O-izopropilidenske derivate 5 i 10, kao i više lipofilnih derivata (jedinjenja 26, 30, 33, 65, ent-30 i ent-33). Konačno, u drugom delu rada, ispitan je uticaj sintetizovanih stiril-laktona na rast odabranih tumorskih ćelijskih linija in vitro.
Enantiodivergent total syntheses of both (+)- and (−)-enantiomers of goniofufurone, 7-epi-goniofufurone and crassalactone C have been accomplished starting from D-glucose. The key steps of the synthe-sis of 7-epi-(+)-goniofufurone were a stereo-selective addition of  phenyl magnesium bromide to a protected dialdose, followed by a stereospecific furano-lactone ring formation by condensation of a partially protected lactole with Meldrum’s acid. The synthesis of (+)-goniofufurone and (+)-crassalactone C required a configurational inversion at C-5 in the common intermediate that was efficiently achieved under the standard Mitsunobu conditions, or alternatively through a sequential oxidation of the benzylic hydroxyl group followed by a stereo-selective reduction with borohydride. A similar approach was applied to the synthesis of the unnatural enantiomers of goniofufurone, 7-epi-goniofufurone and crassalactone C, two novel, conformationally constrained analogues of both (+)- and (−)-goniofufurone (oxetanes 34 and ent-34). as well as the corresponding 7-deoxygenated derivatives (31 and ent-31). We have also developed the first total synthesis of (+)-crassalactone B (2) and an alternative synthesis of (+)-crassalactone C (3) starting from D-glucose. Finally, the synthesized styryl-lactones were evaluated for their antiproliferative activity against a panel of human tumor cell lines.
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Abermil, Nacim. "Organocatalyse asymétrique de la réaction d'aza-Morita-Baylis-Hillman." Paris 11, 2010. http://www.theses.fr/2010PA112184.

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Ce projet scientifique porte sur le développement d'une version organocatalysée énantiosélective de la réaction d'aza-Morita-Baylis-Hillman (aza-MBH). Tout d'abord, la synthèse de nouveaux organocatalyseurs bifonctionnels dérivés de la β-isocupréidine a été réalisée et a permis d'atteindre d'excellents excès énantiomériques dans le cas de l'acrylate de β-naphtyle. La présence d'une quantité catalytique de β-naphtol s'est révéle��e essentielle à l'efficacité de la transformation. Pour la première fois, l'utilisation d'imines aliphatiques a permis de conduire aux adduits de la réaction d'aza-MBH avec de très bonnes énantiosélectivités. Dans un deuxième temps, un phénomène d'énantiodivergence a été identifié dans le cas des alkylvinylcétones. L'inversion de l'induction asymétrique a lieu suivant la présence ou non de β-naphtol, espèce protique achirale. Par la suite, l'emploi d'α-amidosulfones a permis d'augmenter significativement l'efficacité mais également l'énantiosélectivité de la réaction d'aza-MBH dans le cas des imines aliphatiques. Enfin, dans le but d'essayer de mieux comprendre le processus réactionnel, une étude de modélisation moléculaire a été menée avec le docteur Élise Tran
The aim of this study is the development of a highly enantioselective aza-Morita-Baylis-Hillman reaction catalyzed by β-isocupreidine derivatives. First, new bifunctional organocatalysts have been synthesized and efficiently applied to the aza-MBH transformation involving β-naphthyl acrylate. Indeed, high yields and enantioselectivities have been achieved and the presence of a catalytic amount of β-naphthol appears to be essential to the reaction success. Moreover, aliphatic imines have been converted with excellent stereocontrol for the first time. Next, it has been discovered that β-naphthol, an achiral protic additive, was able to invert the enantioselectivity of the aza-MBH transformation ln the case of alkylvinylketones. Then, the use of α-amidosulfones as imine surrogates allow to increase both efficiency and asymmetric induction of the aza-MBH reactio in the case of aliphatic imines. Finally, in order to try to better understand the transformation process, a molecular modelling study has been conducted with Dr Élise Tran
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Tsai, Cheng Che, and 蔡政哲. "Optically Switchable Helicenes for Enantiodivergent Steglich Rearrangement and Deracemization through Complementary Supramolecular Interaction." Thesis, 2016. http://ndltd.ncl.edu.tw/handle/x8c535.

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博士
國立清華大學
化學系
105
In chapter 1, a pseudo-enantiomeric pair of optically switchable helicenes containing a catalytic 4-N-methylaminopyridine (MAP) bottom unit and a C2-symmetric, (10R,11R)-dimethoxymethyl-dibenzosuberane top template was synthesized. The helicenes underwent complementary photoswitching at 290 nm (P/M’, <1/>99) and 340 nm (P/M’, 91/9) and unidirectional, thermo-rotation at 130 oC (P/M’, 100/0). They were utilized to catalyze enantiodivergent Steglich rearrangement of O- to C-acylated azlactones, with formation of either enantiomers with up to 90% ee (R) and 94% ee (S), respectively. In chapter 2, a photoswitchable, racemic helicene derived from 3,7-gallamide-substituted dibenzosuberene and 8-phenyl-α-azo-tetraline was synthesized. Doped with 25% analogues chiral helecene, the racemic helicene underwent photoswitchings at 270 and 335 nm, leading to exclusive formation of complementary enantiomeric helicenes. The amplification of helical chirality was induced by supramolecular co-assembly with doped chiral analogue as evidenced by SEM analysis of forming gel fibers.
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Book chapters on the topic "Enantiodivergent"

1

Doran, Robert. "A Stereoselective Switch: Enantiodivergent Approach to the Synthesis of Isoflavanones." In Asymmetric Synthesis of Bioactive Lactones and the Development of a Catalytic Asymmetric Synthesis of α-Aryl Ketones, 103–25. Cham: Springer International Publishing, 2015. http://dx.doi.org/10.1007/978-3-319-20544-1_5.

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2

Russell, Trisha A., and Edwin Vedejs. "Enantiodivergent Reactions: Divergent Reactions on a Racemic Mixture and Parallel Kinetic Resolution." In Separation of Enantiomers, 217–66. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2014. http://dx.doi.org/10.1002/9783527650880.ch6.

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