Relevant bibliographies by topics / Stereodivergent synthesis

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  1. Journal articles
  2. Dissertations / Theses
  3. Book chapters

Academic literature on the topic 'Stereodivergent synthesis'

Author: Grafiati
Published: 4 June 2021
Last updated: 8 February 2022

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Journal articles on the topic "Stereodivergent synthesis"

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Zhu, Shenqqing, Lingling Chu, and Fang Wang. "Synergistic Catalysis for Stereodivergent Synthesis of trans- and cis-Skipped Dienes." Synlett 31, no. 18 (2020): 1741–46. http://dx.doi.org/10.1055/s-0040-1707190.

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Catalytic, stereoselective synthesis of skipped dienes is an important topic in organic synthesis. Summarized here are the transition-metal-catalyzed stereoselective approaches and a new, photoinduced stereodivergent strategy reported by our group recently. Our strategy utilizes a synergistic photoredox/nickel protocol to enable the cross-electrophile coupling of allylic carbonates and vinyl triflates to construct 1,4-dienes, the stereoselectivity of which was tuned by the triplet energy (E T) photocatalysts employed, offering a convenient and stereodivergent solution to (E)- and (Z)-1,4-dienes from one set of substrates.
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Kazak, Mihail, Martins Priede, Kirill Shubin, Hannah E. Bartrum, Jean-François Poisson, and Edgars Suna. "Stereodivergent Synthesis of Pseudotabersonine Alkaloids." Organic Letters 19, no. 19 (2017): 5356–59. http://dx.doi.org/10.1021/acs.orglett.7b02635.

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Mori, Yuji, and Makoto Suzuki. "Stereodivergent synthesis of 1,3-polyols." Tetrahedron Letters 30, no. 33 (1989): 4387–88. http://dx.doi.org/10.1016/s0040-4039(00)99367-5.

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Pérez, Laura, Ramon Alibés, Pedro de March, Félix Busqué, Marta Figueredo, and Josep Font. "Stereodivergent Synthesis of (+)- and (−)-Isolineatin." Journal of Organic Chemistry 78, no. 9 (2013): 4483–89. http://dx.doi.org/10.1021/jo400487y.

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Wang, Lu, Fuxing Shi, Chaorong Qi та ін. "Stereodivergent synthesis of β-iodoenol carbamates with CO2via photocatalysis". Chemical Science 12, № 35 (2021): 11821–30. http://dx.doi.org/10.1039/d1sc03366b.

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Górski, Bartosz, Dariusz Basiak, Łukasz Grzesiński та Michał Barbasiewicz. "Stereodivergent synthesis of alkenes by controllable syn-/anti-fragmentation of β-hydroxysulfonyl intermediates". Organic & Biomolecular Chemistry 17, № 33 (2019): 7660–63. http://dx.doi.org/10.1039/c9ob01563a.

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Schmidt, Johannes Philipp, та Bernhard Breit. "Transition metal catalyzed stereodivergent synthesis of syn- and anti-δ-vinyl-lactams: formal total synthesis of (−)-cermizine C and (−)-senepodine G". Chemical Science 10, № 10 (2019): 3074–79. http://dx.doi.org/10.1039/c8sc05502e.

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Anderson, James C., Ian B. Campbell, Sebastien Campos, Jonathan Shannon, and Derek A. Tocher. "Stereoselective synthesis of 1,2-diamine containing indolines by a conjugate addition nitro-mannich reaction." Organic & Biomolecular Chemistry 13, no. 1 (2015): 170–77. http://dx.doi.org/10.1039/c4ob01793e.

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The sequential use of the conjugate addition nitro-Mannich reaction, nitro reduction and then Pd-catalyzed intramolecular cyclisation allows the concise, stereodivergent synthesis of complex indolines.
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Sarkale, Abhijeet M., and Chandrakumar Appayee. "Stereodivergent Synthesis of 1-Hydroxymethylpyrrolizidine Alkaloids." Organic Letters 22, no. 11 (2020): 4355–59. http://dx.doi.org/10.1021/acs.orglett.0c01375.

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Schrader, Thomas O., and Marc L. Snapper. "Stereodivergent Synthesis of All 15-F2Isoprostanes." Journal of the American Chemical Society 124, no. 37 (2002): 10998–1000. http://dx.doi.org/10.1021/ja027154u.

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Dissertations / Theses on the topic "Stereodivergent synthesis"

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Toribio, Villarroya Gladis. "Stereodivergent Synthesis of Polyoxygenated Cyclohexanes." Doctoral thesis, Universitat Autònoma de Barcelona, 2011. http://hdl.handle.net/10803/51485.

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Wong, Zackary L. (Zackary Leland). "Copper-catalyzed enantioselective stereodivergent synthesis of amino alcohols." Thesis, Massachusetts Institute of Technology, 2016. http://hdl.handle.net/1721.1/103506.

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Thesis: S.M., Massachusetts Institute of Technology, Department of Chemistry, 2016.<br>Cataloged from PDF version of thesis.<br>Includes bibliographical references (pages 46-50 (first group)).<br>Different stereoisomers of bioactive molecules can have distinct activities in biological systems. For this reason, it is routine procedure in the drug discovery and development process to prepare the full matrix of possible stereoisomers of drug candidates for biological evaluation and to determine the stereochemical purity of these molecules. Despite many recent advances in asymmetric synthesis, the development of general and practical strategies that are fully divergent and give rise to all stereoisomers of products bearing multiple contiguous stereocenters remains a significant challenge. Herein we report a stereodivergent copper-based approach for the expeditious construction of amino alcohols with high levels of chemo-, regio-, diastero- and enantioselectivity. Specifically, these amino alcohol products were synthesized using the sequential copper hydride-catalyzed hydrosilylation and hydroamination of readily available enals and enones. This strategy provides a route to all possible stereoisomers of these amino alcohol products, which contain up to three contiguous stereocenters. Catalyst control and stereospecificity were simultaneously leveraged to attain exceptional control of the product stereochemistry. Beyond the utility of this protocol, the strategy demonstrated here should inspire the development of methods providing complete sets of stereoisomers for other valuable synthetic targets.<br>by Zackary L. Wong.<br>S.M.
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Martinelli, Ada. "Organocatalytic stereodivergent synthesis of β,β-disubstituted-α-aminoacids". Master's thesis, Alma Mater Studiorum - Università di Bologna, 2017. http://amslaurea.unibo.it/13876/.

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In this work, we present an organocatalytic stereodivergent synthesis of β,β-disubstituted-α-aminoacids using arylidene azlactones as starting materials. The developed two step synthesis involves a sequential catalysis approach, in which two different catalysts act sequentially to control the absolute configuration of two different stereocenters. With an accurate selection of the catalysts absolute configuration it is possible to obtain all the stereoisomers of the product. The first synthetic step is a catalytic asymmetric transfer hydrogenation of the azlactone C=C double bond. A Jacobsen type thiourea and a Hantzsch ester were chosen as chiral catalyst and hydride donor, respectively. Different azlactones, Hantzsch esters and thioureas were synthetized and tested in the asymmetric transfer hydrogenation to achieve the best stereoselectivity. The second step involves a dynamic kinetic resolution on the reduced azlactone, through a nucleophilic addition to the carbonyl moiety promoted by a bifunctional chiral catalyst. A wide range of nucleophiles and organocatalysts were tested; the best results were reached with alcohols as nucleophiles and squaramide-based cinchona alkaloids as a chiral catalysts. With the optimized conditions two stereodivergent syntheses were then performed, enabling the selective obtainment of both diastereoisomeric product with high enantioselectivities.
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Riccioli, Riccardo. "Stereodivergent synthesis of β-trifluoromethyl-α- amino acids by sequential catalytic processes". Master's thesis, Alma Mater Studiorum - Università di Bologna, 2018. http://amslaurea.unibo.it/16194/.

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In this work, a sequential organocatalytic process for the stereodivergent synthesis of β-trifluoromethyl-α-amino acids using Erlenmeyer azlactones as starting material is presented. The strategy developed consists of a sequential catalytic approach, employing two catalysts that act independently to control the absolute configuration of two different stereocenters. The first step is a catalytic asymmetric hydrogen transfer of the activated double bond of the azlactone promoted by a Jacobsen type thiourea and Hantzsch ester as hydride donor. The second step involves a nucleophilic addition of an alcohol to the carbonyl moiety controlled by a chiral bifunctional catalyst typically used in the dynamic kinetic resolution of azlactones. The catalyst structure for the second synthetic step was thoroughly investigated in order to maximize the selectivity. Both products were achieved with a good diastereoselectivity and high enantioselectivity. Taking into account the obtained result it was possible to set up an initial study for the feasibility of straightforward one-pot procedure. In conclusion, with this work it was possible to set up a synthetic strategy for the synthesis of all four diastereoisomers starting from the set of starting material.
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Fleary-Roberts, Nadia. "Towards the total synthesis of domoic acid and the isodomoic acids." Thesis, University of Manchester, 2014. https://www.research.manchester.ac.uk/portal/en/theses/towards-the-total-synthesis-of-domoic-acid-and-the-isodomoic-acids(a32fd085-8e09-47b5-b533-ef259b1ae8a2).html.

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Hsiao, Yin-Ting. "Application of the stereodivergent oxy-michael cyclisation to the synthesis of natural products and organocatalytic asymmetric aldol reactions in water." Thesis, University of York, 2017. http://etheses.whiterose.ac.uk/20324/.

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This work outlines two different projects. The first project was the study of a stereodivergent oxy-Michael cyclisation and its application towards the synthesis of natural products, diospongin A, diospongin B and psymberin/ircinistatin A. The α,β-unsaturated thioesters under TBAF-mediated conditions gave the 2,6-trans-tetrahydropyran; under acid-mediated conditions gave the 2,6-cis-tetrahydropyran. The 4-hydroxyl group is crucial for the stereodivergence; when the hydroxyl group was removed or protected the stereodivergence vanished. The second project was the study of (L)-proline benzyl ester-catalysed asymmetric aldol reactions in water. The reaction was carried out in a pH 7 buffered aqueous solution of cyclohexanone and a series of aryl aldehydes to provide anti aldol products in 7-89% ee. The aldol reaction between various ketone donors with 4-nitrobenzaldehyde under the same conditions were also developed to provide products in 13-61% ee.
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Mao, Zhongyi. "Stereodivergent and enantioselective total syntheses of chaetominine-type alkaloids and azaphilic radical cascade cyclization for the synthesis of imidazo-fused heteroaromatics and toward analogs of the 2-Carboxyl-6-HydroxyOctahydroIndole (CHOI) Unit." Thesis, Paris 6, 2017. http://www.theses.fr/2017PA066449/document.

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Les composés azotés ont un grand intérêt car cet élément se retrouve dans la plupart des produits naturels et pharmaceutiques, de sorte que le développement de méthodes efficaces pour leur préparation est hautement souhaitable. Tout d'abord, une méthode stéréodivergente et énantiosélective a été développée pour la synthèse totale des alcaloïdes de type chaetominine, y compris les structures proposées de la (-)-pseudofischerine, de l’(-)-aniquinazoline D et de l’(-)-isochaetominine, de l’(-)-isochaetominines A-C, de la (+)-14-epi-isochaetominine C, ainsi que les quatre stéréoisomères jusqu'ici inconnus de l'isochaetominine C. A la lumière de nos travaux de synthèse, les structures de la (-)-pseudofischerine naturelle et l’(-)-aniquinazoline D ont été révisées comme l’(-)-isochaetominine C, et la structure de l’(-)-isochaetominine naturelle a été révisée comme la (-)-11-epi-chaetominine. Ensuite, une réaction de cyclisation en cascade de radicaux azaphiles a été développée conduisant à une synthèse efficace d'hétéroaromatiques de type imidazo-accolés à partir de carbamates N-hétéroaryl-O-propargyliques facilement disponibles. La synthèse électrochimique organocatalysée est généralisable, tolère de nombreux groupes fonctionnels, et se déroule dans des conditions douces sans besoin de catalyse par les métaux de transition, ni d'oxydants. Enfin, deux approches à des analogues de l'unité CHOI ont été développées. Les étapes clés de la de synthèse sont basées sur la C-allylation et la N-allylation palladocatalysées, qui permettent la transformation d’un substrat bis-allylique cyclique en un hexahydroindole. En fonction de la stratégie appliquée, la position de la fonction alcène de l'hexahydroindole peut se retrouver sur des positions différentes du squelette. L’homologation d’un atome de carbone suivie d'une époxydation ou d'une syn-dihydroxylation des intermédiaires bicycliques résultants fournissent les analogues CHOI désirés<br>Nitrogen-containing compounds have a great interest as this element is found in natural products and drugs, thus the development of efficient methods for their preparation is highly desirable. First, a stereodivergent and enantioselective method has been developed for the total syntheses of chaetominine-type alkaloids including the proposed structures of (-)-pseudofischerine, (-)-aniquinazoline D and (-)-isochaetominine, (-)-isochaetominines A–C, (+)-14-epi-isochaetominine C, as well as the four hitherto unknown stereoisomers of isochaetominine C. The structures of natural (-)-pseudofischerine and (-)-aniquinazoline D have been revised as (-)-isochaetominine C and the structure of the natural (-)-isochaetominine have been revised to (-)-11-epi-chaetominine based on our synthetic efforts. Next, an azaphilic radical cascade cyclization reaction has been developed leading to the efficient synthesis of imidazo-fused heteroaromatics from easily available N-heteroaryl-O-propargyl carbamates. The organocatalyzed electrochemical synthesis has a broad scope, tolerates many common functional groups, and proceeds under mild conditions without the need of transition-metal catalysis or chemical oxidant. Finally, two approaches toward analogs of the CHOI unit have been developed. The key steps of the synthetic route were based on Pd-catalyzed C-allylation and N-allylation, which converted a cyclic bis-allylic substrate into a hexahydroindole scaffold. Depending on the strategy applied, the position of alkene moiety of the resulting hexahydroindole can be obtained at different positions. One-carbon homologation followed by epoxidation or syn-dihydroxylation of the resulting bicyclic intermediates afforded the desired CHOI analogues
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Antien, Kevin. "Développement de nouveaux réactifs iodés hypervalents chiraux hélicéniques. Synthèse collective stéréodivergente d’alcaloïdes de Securinega." Thesis, Bordeaux, 2018. http://www.theses.fr/2018BORD0349/document.

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La chimie des composés iodés hypervalents, ou organoiodanes, suscite un engouement croissant de la part de la communauté scientifique depuis maintenant près de 30 ans. Les efforts de recherche sont de nos jours orientés de manière prépondérante vers des applications en synthèse asymétrique, principalement au travers de l’utilisation d’architectures organoiodées chirales. À ce jour, seules les chiralités centrales et axiales sont exploitées dans l’élaboration de tels objets. L’emploi d’iodanes achiraux (i.e. en synthèse asymétrique) en présence d’additifs chiraux a par ailleurs été largement négligé par la communauté. La chiralité hélicoïdale est incarnée en chimie organique par les hélicènes. Ces composés polyaromatiques sont des objets fascinants de par leurs propriétés structurelles, électroniques et chiroptiques hors du commun. Ils sont le centre d’une attention considérable dans de nombreux domaines de recherches allant de la catalyse asymétrique à l’élaboration de diodes électroluminescentes organiques. Jamais la chiralité hélicoïdale n’a été exploitée en chimie de l’iode hypervalent. Ces travaux de thèse traitent en premier lieu de l’élaboration d’une méthodologie asymétrique de désaromatisation oxygénante de phénols faisant usage d’un iodane-3 achiral en présence d’un agent de transfert de phase issu des alcaloïdes du Quinquina. Dans une seconde partie de ces travaux est abordée la synthèse asymétrique d’un nouvel iodoarène hélicénique et ses premières applications dans des réactions de désaromatisation oxygénante de phénols. Cet ouvrage traite également dans un troisième chapitre d’une synthèse totale, collective et stéréodivergente de 12 alcaloïdes de Securinega. Il s’agit d’une classe métabolites secondaires retrouvés dans de multiples plantes des genres Securinega (Flueggea), Phyllanthus, Margaritaria et Breynia de la famille Phyllanthaceae. Depuis près d’un demi-siècle, la biogénèse de ces molécules naturelles demeure partiellement incomprise. La synthèse développée dans ce travail a pour vocation d’améliorer la compréhension du mécanisme biosynthétique à l’origine de ces substances. Il a ainsi été établi qu’une étape clé de condensation aldolique pourrait permettre d’expliquer la stéréodivergence observée dans la nature<br>Hypervalent iodine chemistry has been arousing the interest of the scientific community for the last 30 years. Research efforts are now mainly directed towards applications in asymmetric synthesis, notably through the use of chiral organoiodine scaffolds. To this end, solely central and axial chiralities have been exploited to construct such objects. The use of achiral iodanes (i.e. hypervalent organoiodine compounds) in asymmetric synthesis has been largely neglected by the community. Helical chirality in organic synthesis is mainly found in polyaromatic compounds known as helicenes. These molecules exhibit fascinating structural, electronic and chiroptical properties. They are the center of considerable attention across many fields of research, spanning from asymmetric catalysis to organic light-emitting diodes. Helical chirality has never been exploited in the field of hypervalent iodine chemistry. In the first part of this doctoral work, a methodology for the asymmetric oxygenative dearomatization of phenols by an achiral 3-iodane in the presence of a Cinchona-alkaloid-based phase transfer agent was developed. The second part of this manuscript details the synthesis of a new helicenic organoiodine compound and its application to oxygenative phenol dearomatization reactions. In the last chapter of this doctoral dissertation is described the total, collective and stereodivergent synthesis of 12 Securinega alkaloids. These natural products are commonly found in plants belonging to the genera Securinega (Flueggea), Phyllanthus, Margaritaria and Breynia of the Phyllanthaceae family. Even after little less than half a century of research, the real biogenetic pathway used by nature to construct these molecules is still only partly understood. The chemical synthesis developed in this doctoral work provides a better understanding of the biosynthetic mechanism. It was established in the course of this work that a key aldol condensation step could shed light upon the stereodivergence observed in nature
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Strand, Daniel. "Methods for Asymmetric Olefination Reactions; Development and Application to Natural Product Synthesis." Doctoral thesis, Stockholm : Chemical Science and Engineering, KTH, 2006. http://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-4088.

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Book chapters on the topic "Stereodivergent synthesis"

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Shao, Z., and Y. H. Deng. "2.1.1 General Principles of Metal/Organocatalyst Dual Catalysis." In Dual Catalysis in Organic Synthesis 2. Georg Thieme Verlag, 2020. http://dx.doi.org/10.1055/sos-sd-232-00002.

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AbstractMetal/organocatalyst dual catalysis is a privileged catalytic strategy which involves both a metal-based catalyst and an organocatalyst to catalyze the organic transformation. Based on the type of activation of substrates with both catalysts, there are seven kinds of dual catalysis; namely cooperative catalysis, cascade catalysis, sequential catalysis, double activation catalysis, restorative catalysis, bifunctional catalysis, and multiple relay catalysis. The generic activation of the metal-based catalyst and the organocatalyst applied in the dual-catalytic system is summarized. In these dual-catalytic approaches, the advantages of both metal catalysis and organocatalysis are converged to achieve many transformations that were previously inaccessible or challenging by any single-catalyst paradigm, to develop new reactions, to discover unique reaction mechanisms, and even to allow for stereodivergent synthesis.
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Toyooka, Naoki, Maiko Okumura, and Hideo Nemoto. "Stereodivergent Process for the Synthesis of the Decahydroquinoline-type Dendrobated Alkaloids." In 19th International Congress on Heterocyclic Chemistry. Elsevier, 2003. http://dx.doi.org/10.1016/b978-0-08-044304-1.50336-1.

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Taber, Douglass F. "Synthesis of Naturally Occurring Cyclic Ethers: Boivivianin B (Murakami), SC- Δ 13 -9-IsoF (Taber), Brevisamide (Panek, Lindsley,Ghosh), Gambierol (Mori)." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0050.

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The challenge of controlling the relative and absolute configuration of highly substituted cyclic ether-containing natural products continues to stimulate the development of new synthetic methods. Masahiro Murakami of Kyoto University showed (J. Org. Chem. 2009, 74, 6050) that Rh-mediated addition of an aryl boronic acid to 1 proceeded with high syn diastereocontrol, giving 3. This set the stage for Au-mediated rearrangement, leading to 4. We found (J. Org. Chem. 2009, 74, 5516) that asymmetric epoxidation of 5 followed by exposure to AD-mix could be used to prepare each of the four diastereomers of 6. We carried 6 on the isofuran 7, using a stereodivergent strategy that allowed the preparation of each of the 32 enantiomerically pure diastereomers of the natural product. Following up on the synthesis of brevisamide 16 described (Organic Highlights, November 16, 2009) by Kazuo Tachibana of the University of Tokyo, three groups reported alternative total syntheses. James S. Panek of Boston University prepared (Organic Lett. 2009, 11, 4390) the cyclic ether of 16 by addition of the enantiomerically pure silane 9 to 8. Craig W. Lindsley of Vanderbilt University used (Organic Lett. 2009, 11, 3950) SmI2 to effect the cyclization of 11 to 12. Arun K. Ghosh of Purdue University employed (Organic Lett. 2009, 11, 4164) an enantiomerically pure Cr catalyst to direct the absolute configuration in the hetero Diels-Alder addition of 14 to 13. Rubottom oxidation of the enol ether so formed led to the α-hydroxy ketone 15. Yuji Mori of Meijo University described (Organic Lett. 2009, 11, 4382) the total synthesis of the Gambierdiscus toxicus ladder ether gambierol 19. A key strategy, used repeatedly through the sequence, was the exo cyclization of an epoxy sulfone, illustrated by the conversion of 17 to 18. The epoxy sulfones were prepared by alkylating the anions derived from preformed epoxy sulfones such as 20.
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Lambert, Tristan H. "C–O Ring Formation." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0049.

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A reductive radical cyclization of tetrahydropyran 1 to form bicycle 2 using iron(II) chloride in the presence of NaBH4 was reported (Angew. Chem. Int. Ed. 2012, 51, 6942) by Louis Fensterbank and Cyril Ollivier at the University of Paris and Anny Jutand at the Ecole Normale Supérieure. The enantioselective conversion of tetrahydrofuran 3 to spirocycle 5 via iminium ion-catalyzed hydride transfer/cyclization was developed (Angew. Chem. Int. Ed. 2012, 51, 8811) by Yong-Qiang Tu at Lanzhou University. Daniel Romo at Texas A&amp;M University showed (J. Am. Chem. Soc. 2012, 134, 13348) that enantioenriched tricyclic β-lactone 8 could be readily prepared via dyotropic rearrangement of the diketoacid 6 under catalysis by chiral Lewis base 7. A dyotropic rearrangement was also utilized (Angew. Chem. Int. Ed. 2012, 51, 6984) by Zhen Yang at Peking University, Tuoping Luo at H3 Biomedicine in Cambridge, MA, and Yefeng Tang at Tsinghua University for the conversion of 9 to the bicyclic lactone 10. In terms of the enantioselective synthesis of β-lactones, Karl Scheidt at Northwestern University found that NHC catalyst 12 effects (Angew. Chem. Int. Ed. 2012, 51, 7309) the dynamic kinetic resolution of aldehyde 11 to furnish the lactone 13 with very high ee. Meanwhile, Xiaomeng Feng at Sichuan University has developed (J. Am Chem. Soc. 2012, 134, 17023) a rare example of an enantioselective Baeyer-Villiger oxidation of 4-alkyl cyclohexanones such as 14. The diastereoselective preparation of tetrahydropyran 18 by Lewis acid-promoted cyclization of cyclopropane 17 was accomplished (Org. Lett. 2012, 14, 6258) by Jin Kun Cha at Wayne State University. Stephen J. Connon at the University of Dublin reported (Chem. Commun. 2012, 48, 6502) the formal cycloaddition of aryl succinic anhydrides such as 18 with aldehydes to produce γ-butyrolactones, including 20, in high ee. The stereodivergent cyclization of 21 via desilylation-induced heteroconjugate addition to produce the complex tetrahydropyran 22 was discovered (Org. Lett. 2012, 14, 5550) by Paul A. Clarke at the University of York. Remarkably, while TFA produced a 13:1 diastereomeric ratio in favor of the cis diastereomer 22, the use of TBAF resulted in complete reversal of diastereoselectivity.
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Benkoski, Léa, and Tristan H. Lambert. "Construction of Multiple Stereocenters." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0039.

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Erick M. Carreira at ETH Zürich reported (Science 2013, 340, 1065) the enantiose­lective α-allylation of aldehyde 1 with alcohol 2 to produce 3 using a dual catalytic system involving a chiral iridium complex and amine 5. This stereodivergent method allows access to all of the possible stereoisomers of 3. In a conceptually related proc­ess, John F. Hartwig at the University of California, Berkeley reported (J. Am. Chem. Soc. 2013, 135, 2068) the highly stereoselective allylic alkylation of azlactone 6 with allylic carbonate 7 catalyzed by a combination of Ir(cod)Cl₂, ligand 9, and racemic silver phosphate 10. An enantioselective three-component Mannich-type reaction of tert-butyl diazo­acetate, aniline, and imine 11 to produce α,β-bis(arylamino) acid derivative 13 under dual catalysis with Rh₂(OAc)₄ and acid 12 was developed (Synthesis 2013, 45, 452) by Wenhao Hu at the Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development. Keiji Maruoka at Kyoto University reported (Chem. Commun. 2013, 49, 1118) a one-pot cross double-Mannich reaction of acetylalde­hyde 14, and imines 16 and 17 using axially chiral amino sulfonamide 15 to obtain densely functionalized 1,3-diamine 18 as a single stereoisomer. Jeffrey S. Johnson at the University of North Carolina at Chapel Hill reported (Org. Lett. 2013, 15, 2446) the asymmetric synthesis of enantioenriched anti-α-hydroxy-β-amino acid derivative 21 from 19 by treatment with oxone followed by catalytic hydrogenation using Ru(II) complex 20. Naoya Kumagai and Masakatsu Shibasaki at the Institute of Microbial Chemistry found (Org. Lett. 2013, 15, 2632) that a sil­ver complex of bisphosphine 24 effected a syn-selective and highly enantioselective Mannich-type reaction of aldimine 22 and α-sulfanyl lactone 23 to furnish the stereo­diad 25 with very high ee. The enantioselective homocrotylation of octanal 26 with cyclopropylcarbinylbo­ronate 27 to produce alcohol 28 with high ee was disclosed (J. Am. Chem. Soc. 2013, 135, 82) by Isaac J. Krauss at Brandeis University with computational studies pro­vided by Kendall N. Houk at UCLA. Benjamin List at the Max-Planck-Institut für Kohlenforschung reported (J. Am. Chem. Soc. 2013, 135, 6677) the enantioselective epoxidation of cyclohexenone 29 utilizing cinchona alkaloid- derived catalyst 30.
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