Relevant bibliographies by topics / Spirocycle

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  1. Journal articles
  2. Dissertations / Theses
  3. Book chapters
  4. Conference papers

Academic literature on the topic 'Spirocycle'

Author: Grafiati
Published: 4 June 2021
Last updated: 13 February 2022

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Journal articles on the topic "Spirocycle"

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Wollenweber, Markus, Reinhart Keese, and Helen Stoeckli-Evans. "Synthesis of Spirocyclic Aminosilanes with Electron Withdrawing Substituents at Nitrogen." Zeitschrift für Naturforschung B 53, no. 2 (February 1, 1998): 145–48. http://dx.doi.org/10.1515/znb-1998-0202.

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Abstract The first synthesis of spirocyclic tetrasulfonamidosilanes is described. According to the X-Ray structure analysis of the most stable tetratosylamidosilane obtained the Silicon is bonded to four Nitrogen atoms in a spirocycle and surrounded by four Oxygen atoms which are located above the planes of the SiN4 tetrahedron.
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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 (July 1, 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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Ji, Yanling, Xianghong He, Cheng Peng, and Wei Huang. "Recent advances in the synthesis of C2-spiropseudoindoxyls." Organic & Biomolecular Chemistry 17, no. 11 (2019): 2850–64. http://dx.doi.org/10.1039/c8ob03122c.

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Klika Škopić, Mateja, Suzanne Willems, Bernd Wagner, Justin Schieven, Norbert Krause, and Andreas Brunschweiger. "Exploration of a Au(i)-mediated three-component reaction for the synthesis of DNA-tagged highly substituted spiroheterocycles." Org. Biomol. Chem. 15, no. 40 (2017): 8648–54. http://dx.doi.org/10.1039/c7ob02347b.

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Xue, Bingxiang, Shikuan Su, Yongmei Cui, Youwen Fei, Xueshun Jia, Jian Li, and Jianhui Fang. "Phosphine-mediated sequential annulations of allenyl ketone and isocyanide: a bicyclization strategy to access a furan-fused eight-membered ring and a spirocycle." Chemical Communications 55, no. 81 (2019): 12180–83. http://dx.doi.org/10.1039/c9cc06267j.

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Huang, Ji-Rong, Liu Qin, Yu-Qin Zhu, Qiang Song, and Lin Dong. "Multi-site cyclization via initial C–H activation using a rhodium(iii) catalyst: rapid assembly of frameworks containing indoles and indolines." Chemical Communications 51, no. 14 (2015): 2844–47. http://dx.doi.org/10.1039/c4cc07125e.

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Tandem multi-site cyclization triggered by Rh(iii)-catalyzed C–H activation has been achieved for highly efficient synthesis of spirocycle indolin-3-one (C2-cyclization), benzo[a]carbazole (C3-cyclization) and an unusual indoxyl core (N1-cyclization).
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Farat, Oleg, Svetlana Varenichenko, Ekaterina Zaliznaya, and Victor Markov. "REARRANGEMENT OF SUBSTITUTED 1,3-BENZOXAZINES INTO XANTHENE-TYPE COMPOUNDS." Ukrainian Chemistry Journal 86, no. 2 (February 5, 2020): 111–22. http://dx.doi.org/10.33609/0041-6045.86.2.2020.111-122.

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The rearrangement patterns of new 1,3-benzoxazines derivatives obtained by condensation of substituted salicylamides with cyclic ketones under the influence of Vilsmeier-Haack reagent has been studied. The influence of angel strain in a 4-membered spirocycle prevents the rearrangement of spiro [1,3-benzoxazine-2,1'-cyclobutan]-4(3H)-one under the action of a formylating agent. 1,3-Benzoxazines derivatives with ring sizes from 5- to 8-membered under the action of a formylating agent have formed formylxanthene derivative. Their formation reaction rate depends on the presence of electronegativity substituents at positions C-6 and C-8 of the aromatic cycle, as well as in the spiroring. In this work, we presented an effective method for the synthesis of formyl derivatives of xanthenes based on readily available salicylamide. It was found that (spiro[1,3-benzoxazine-2,1'-cyclobutan]-4(3H)-one) does not rearrange even under prolonged heating due to the spirocycle strain. The presence of bromine or iodine atoms at positions C-6 and C-8 of the aromatic cycle of 1,3-benzoxazines makes the reaction more difficult, which requires more harsh synthesis conditions.
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Jiang, Chongguo, Sijia Chen, Jianxian Gong, and Zhen Yang. "Synthetic Study Toward the 4,5-Spirocycle Skeleton of Phainanoids." Acta Chimica Sinica 78, no. 9 (2020): 928. http://dx.doi.org/10.6023/a20060198.

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Bassindale, Martin J., Peter Hamley, Andreas Leitner, and Joseph P. A. Harrity. "Spirocycle assembly through selective tandem ring closing metathesis reactions." Tetrahedron Letters 40, no. 16 (April 1999): 3247–50. http://dx.doi.org/10.1016/s0040-4039(99)00375-5.

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Tkachuk, Anna V., Sergey V. Kurbatov, Pavel G. Morozov, and Gennadiy S. Borodkin. "The first dipolar spirocycle based on 10-(benzylamino)colchicine." Chemistry of Heterocyclic Compounds 51, no. 10 (October 2015): 948–50. http://dx.doi.org/10.1007/s10593-015-1803-5.

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Dissertations / Theses on the topic "Spirocycle"

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Ferdenzi, Antoine. "Approche des synthèses de la saraïne A et de la misénine, alcaloïdes marins extraits de l'éponge reniera saraï, à partir d'une hypothèse biogénétique commune." Paris 11, 2006. http://www.theses.fr/2006PA112242.

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Peneau, Augustin. "Vers la synthèse totale du 13-desméthyle spirolide C. Synthèse d’hétérocycles par activation C–H catalysée au Rh(III)." Thesis, Université Paris-Saclay (ComUE), 2018. http://www.theses.fr/2018SACLS410/document.

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Certaines phycotoxines marines de la famille des spiroimines, comme la gymnodimine et les spirolides sont produites par des dinoflagellés et se concentrent dans les mollusques filtreurs. Puis, par transport vectoriel, elles peuvent atteindre les animaux marins et les êtres humains. Des études biologiques ont montré que ces toxines sont de puissants antagonistes des récepteurs nicotiniques de l’acétylcholine (nAChRs) et qu’elles présentent une spécificité modérée pour des sous-types de récepteurs. Au laboratoire, nous nous intéressons à la synthèse totale du 13-desméthyle spirolide C, dans le but de produire une plus grande quantité de cette molécule (que par extraction) afin d'étudier plus en détail son activité biologique. Afin d’atteindre ce but, deux stratégies seront présentées. La première faisant intervenir une réaction-clef de décarboxylation allylante asymétrique, permettant la formation stéréosélective d’un centre quaternaire. La seconde approche utilise une réaction de Diels-Alder intermoléculaire pour construire le même motif. Au cours de ces dernières années, les récents développements dans le domaine des couplages organométalliques ont permis de s’affranchir de la préfonctionnalisation d’une liaison C_H avant sa transformation en liaison C_C ou C_hétéroatome, par l’utilisation de catalyseurs à base de métaux de transition. Afin de pallier ce problème, une approche généralement employée, consiste à utiliser la proximité spatiale d’un hétéroatome chélatant (N, O, etc.), appelé groupement directeur (GD), qui permet de diriger la réaction vers une liaison C_H spécifique. Nous avons étudié l’application d’une réaction de type Heck dans la synthèse de squelettes de molécules biologiquement actives. Dans un second chapitre de ce manuscrit seront détaillés les récents avancements dans la synthèse d’hétérocycles par activation C_H, catalysée au rhodium (III). Ainsi, la synthèse de spirocycles carbonés, de spiropipéridines et d’azépinones seront présentés, accompagnées des considérations mécanistiques de ces réactions
Some marine shellfish toxins in the spiroimine family like gymnodimine and spirolides are produced by dinoflagellates and can be transferred and concentrated in seafood then by vectorial transport they can reach marine animals and humans. Biological studies have shown that these toxins are potent antagonists of the nicotinic acetylcholine receptors (nAChRs) and have a moderate selectivity for subtypes receptor. In the laboratory, we are interested in the total synthesis of gymnodimine and 13-desmethyl spirolide C in order to produce a larger quantity of these molecules (compared to isolation from dinoflagellates) to further investigate their biological activities. In this regard, we developed two complementary approaches to access the spiroimine pattern of these molecules. The first one is based on a decarboxylative asymmetric allylic alkylation reaction. The second uses an intermolecular Diels-Alder reaction.With the need of more sophisticated scaffolds for medicinal chemistry or total synthesis, the development of appropriate ortho-directed C_H activation reactions have proven recently to be crucial. Herein, we propose two simple and efficient intramolecular cyclisation reactions, involving a methoxy-amide directing group and a Rh(III)-catalysis. Synthesis of spiropiperidines and azepinones are presented
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Powell, Nicola Helen. "Novel oxetane-containing spirocycles and peptidomimetics." Thesis, University of Warwick, 2014. http://wrap.warwick.ac.uk/66720/.

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This thesis describes work focused on the use of oxetane rings as isosteres and incorporation of this functional group into pharmaceutically relevant scaffolds. Chapter 1 describes work directed towards the synthesis of 1,5-dioxaspiro[2.3]hexanes via three different strategies, namely ring-closure to form the oxetane ring, Corey epoxidation of the corresponding 3-oxetanones, and epoxidation of the corresponding 3-methylene oxetane. Nucleophilic ring-opening of substituted 1,5-dioxaspiro[2.3]hexanes to give amino acid type isosteres is also investigated. Chapter 2 details the synthesis of novel oxetane-containing peptidomimetics. A ‘one-pot’ conjugate addition process from commercially available 3-oxetanone to give nitro dipeptide precursors in good yields was developed. Various methods for the reduction of the nitro group were explored to optimise the synthesis of the corresponding amine. Amide coupling, followed by deprotection, gave peptidomimetics containing the oxetane at the C-terminus and mid-chain in good yields over the 3 steps, whilst an N-terminus oxetane peptidomimetic was obtained in 45% yield through hydrogenation of the conjugate addition product. X-ray diffraction studies, alongside molecular dynamics simulations, provided structural insights into these new oxetane-containing peptidomimetics. Detailed experimental procedures for the synthesis of all novel compounds are described in Chapter 3.
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Hilmey, David George. "Synthesis and study of heteroatomic spirocyclic scaffolds." Columbus, Ohio : Ohio State University, 2006. http://rave.ohiolink.edu/etdc/view?acc%5Fnum=osu1141334542.

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Ferrari, Frank D. "Flexible synthesis of spirocyclic pyrans and piperidines." Thesis, University of Glasgow, 2012. http://theses.gla.ac.uk/3829/.

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Spirocyclic piperidines and spirocyclic pyrans are prevalent throughout nature, often appearing in natural products which exhibit exciting biological activities. Notable examples of spirocyclic piperidine-containing biologically active natural products are halichlorine, pinnaic acid and tauropinnaic acid. Despite their structural similarity, halichlorine and the pinnaic acids were isolated from separate organisms; halichlorine was isolated from extracts of the marine sponge Halichondria okadai while both pinnaic acid and tauropinnaic acid were isolated from the Okinawan bivalve mollusc Pinna muricata. The complex hybrid molecule polymaxenolide contains a representative spirocyclic pyran core. The biological profile of polymaxenolide is not yet known, however its hybrid origins have rendered it a target of significant interest. The work described herein details the development of a methodology capable of accessing both spirocyclic pyran and spirocyclic piperidine core structures from a common cyclic tertiary furfuryl alcohol intermediate. The key spirocycle forming step involves the oxidative rearrangement of cyclic tertiary furfuryl alcohols and amines for the synthesis of spirocyclic pyrans and piperidines, respectively. Efforts towards the synthesis of a complex, africanane-derived Southern fragment, with the intention of applying this methodology towards the synthesis of polymaxenolide are reported. This methodology has been further elaborated to complete an asymmetric synthesis of the upper framework of an oxa-analogue of pinnaic acid. The potential for a spectator protecting group free synthesis of pinnaic acid was also explored and the synthesis of an advanced intermediate is also reported.
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Prail, J. "The synthesis and biohydroxylation of spirocyclic amides." Thesis, University of Exeter, 1991. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.293090.

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Pancholi, Alpa Kishor. "Synthesis of substituted azetidines and spirocyclic diazetidines." Thesis, University of Warwick, 2017. http://wrap.warwick.ac.uk/102606/.

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Chapter 1 begins with an introduction to azetidines, including a discussion of the methodologies for their synthesis, their applications, relevance in natural products and as building blocks in medicinal chemistry. It then describes the development of a new asymmetric route to 2-substituted azetidin-3-ones using Enders’ SAMP/RAMP auxiliary. A one-pot process was developed involving the metalation of SAMP hydrazones of N-Boc-azetidin-3-one, alkylation and subsequent in situ hydrolysis to give the substituted products. Various bases and reaction conditions were explored to find optimal conditions for maximal yield and enantioselectivity. A representative range of electrophiles were screened including alkyl, allyl and benzyl halides and carbonyl compounds, producing enantioselectivities of up to 85% ee. Multiple substitution on the azetidin-3-one ring was briefly explored by repetition of the alkylation/hydrolysis sequence. Derivitisation by way of Pictet-Spengler reactions was used to confirm the absolute configuration at the newly created stereocentre. Chapter 2 begins with an introduction to 1,2-diazetidines outlining methods for their synthesis, before introducing the relevance of these nitrogen spirocycles. This chapter then describes two routes for the synthesis of these novel spirocyclic 1,2- diazetidines by (i) formation of the diazetidine ring and (ii) functionalisation of a range of 3-methylene-1,2-diazetidines including differentially protected variants. The diazetidines were subjected to dichloro- and difluorocyclopropanation with the latter achieved in high yields. Additionally, reactions with tetracyanoethylene by way of highly asynchronous [2π+2π] cycloadditions proceeded in near quantitative yield. In this way, a range of novel 4,5-diazaspiro[2.3]hexane and 1,2- diazaspiro[3.3]heptane spirocycles were produced. Chapter 3 details the experimental procedure and characterisation for all the novel compounds synthesised.
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Branan, Bruce Monroe. "The chemistry of polycyclic and spirocyclic compounds /." The Ohio State University, 1994. http://rave.ohiolink.edu/etdc/view?acc_num=osu1487849696968107.

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Main, Calver A. "Novel titanium carbenoid reagents : diversity orientated synthesis of indoles and spirocycles." Thesis, University of Glasgow, 2008. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.502007.

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A new synthetic strategy for the preparation of a 96-member library of 2,5-disubstituted indoles involving traceless cleavage from resin is presented. A boronate-bearing titanium alkylidene was prepared and used to convert 8 resin-bound esters into immobilised enol ethers. Cleavage from resin in mild acid with concomitant cyclisation yielded boronate-bearing indoles. Capitalising on the immobilised boronate functionality in enol ethers, Suzuki cross-coupling reactions were performed with 12 aryl iodides to give a 96-member library after cleavage from resin with mild acid, 79 members of the library were confirmed to be 2,5-disubstituted indoles. Also reported is the use of tertiary butyllithium and 2-isopropoxy-4,4,i,5-tetramethyl-l,3,2-dioxaborolane to convert an aiyl bromide into an arylboronate in the presence of a dithiane, with simultaneous reduction of an aryl azide to an amine. In a similar route, we synthesised dithiane for the attempted conversion of resin-bound esters into functionalised 7-azaindoles after cleavage from resin. Further investigation with a different ortho-nitrogen protecting group may yet prove successful.
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Bird, P. M. "Stereocontrol in the synthesis of substituted spirocyclic ethers." Thesis, University of Cambridge, 1997. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.596658.

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This thesis describes the synthesis of spirocyclic ethers with substituents in both rings. The strategy employed is considered in stepwise manner starting with the two-step synthesis of the substituted cyclic α-phenylsulfanylcarbaldehydes A and B from the corresponding cyclic ketones, paying particular attention to the stereoselectivity in the first step and the stereospecificity of the second. Simple aldol reactions of these aldehydes with ester and ketone enolates are reported, along with the conversion of the aldol products C to (1,3)-diols D by reduction (including the[1,3]-stereoselective reduction of β-hydroxyketones) or addition of an organometallic reagent. The stereospecific cyclisation of these diols to the targeted spirocyclic ethers E was achieved by treatment with catalytic amounts of p-touenesulfonic acid. Elucidation of the stereochemistry of these tetrahydrofurans and their precursors - and the implications of these assignments - by the examination of 2-D NMR spectra is discussed.
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Book chapters on the topic "Spirocycle"

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Li, Jie Jack, and Minmin Yang. "Spirocyclic Piperidines." In Drug Discovery with Privileged Building Blocks, 251–57. Boca Raton: CRC Press, 2021. http://dx.doi.org/10.1201/9781003190806-28.

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Li, Jie Jack, and Minmin Yang. "Spirocyclic Pyrrolidines." In Drug Discovery with Privileged Building Blocks, 259–67. Boca Raton: CRC Press, 2021. http://dx.doi.org/10.1201/9781003190806-29.

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Sridhar, Perali Ramu. "Carbohydrate-Derived Spiroketals and Spirocyclic Lactones." In Topics in Heterocyclic Chemistry, 105–36. Cham: Springer International Publishing, 2019. http://dx.doi.org/10.1007/7081_2019_32.

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Brimble, Margaret A., and Louise A. Stubbing. "Synthesis of 5,6- and 6,6-Spirocyclic Compounds." In Synthesis of Saturated Oxygenated Heterocycles I, 189–267. Berlin, Heidelberg: Springer Berlin Heidelberg, 2013. http://dx.doi.org/10.1007/978-3-642-41473-2_5.

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Russel, Jonathon S. "Oxindoles and Spirocyclic Variations: Strategies for C3 Functionalization." In Topics in Heterocyclic Chemistry, 397–431. Berlin, Heidelberg: Springer Berlin Heidelberg, 2010. http://dx.doi.org/10.1007/7081_2010_50.

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Soto, Martín, Humberto Rodríguez-Solla, and Raquel Soengas. "Recent Advances in the Chemistry and Biology of Spirocyclic Nucleosides." In Topics in Heterocyclic Chemistry, 171–213. Cham: Springer International Publishing, 2019. http://dx.doi.org/10.1007/7081_2019_31.

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Bari, Shamsher S., and Aman Bhalla. "Spirocyclic β-Lactams: Synthesis and Biological Evaluation of Novel Heterocycles." In Heterocyclic Scaffolds I, 49–99. Berlin, Heidelberg: Springer Berlin Heidelberg, 2010. http://dx.doi.org/10.1007/7081_2009_8.

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Alcaide, Benito, and Pedro Almendros. "Novel Aspects on the Preparation of Spirocyclic and Fused Unusual β-Lactams." In Heterocyclic Scaffolds I, 1–48. Berlin, Heidelberg: Springer Berlin Heidelberg, 2010. http://dx.doi.org/10.1007/7081_2009_7.

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Leeper, Finian J. "The Evidence for a Spirocyclic Intermediate in the Formation of Uroporphyrinogen III by Cosynthase." In Ciba Foundation Symposium 180 - The Biosynthesis of the Tetrapyrrole Pigments, 111–30. Chichester, UK: John Wiley & Sons, Ltd., 2007. http://dx.doi.org/10.1002/9780470514535.ch7.

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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&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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Conference papers on the topic "Spirocycle"

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Li, Hongcheng, Jiping Liu, and Jiayi Zhao. "A Novel Spirocyclic Halogen-Free Flame Retardant: Synthesis and Flammability Characteristics in Epoxy Resin Composites." In 2015 International Conference on Advanced Engineering Materials and Technology. Paris, France: Atlantis Press, 2015. http://dx.doi.org/10.2991/icaemt-15.2015.92.

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