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Relevant bibliographies by topics / Cyclopropyl chemistry

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Academic literature on the topic 'Cyclopropyl chemistry'

Author: Grafiati

Published: 4 June 2021

Last updated: 5 February 2022

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Journal articles on the topic "Cyclopropyl chemistry"

1

Tortosa, Mariola, Víctor Martín-Heras, and Alejandro Parra. "Cyclopropyl- and Cyclobutylboronates and -silanes: A Stereoselective Approach." Synthesis 50, no. 03 (2017): 470–84. http://dx.doi.org/10.1055/s-0036-1589133.

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Chiral cyclopropyl- and cyclobutylboronic esters and -silanes have become attractive intermediates for the preparation of functionalized small rings. This review highlights the stereoselective methods developed for their preparation, including both diastereo- and enantioselective approaches.1 Introduction2 Stereoselective Synthesis of Cyclopropyl- and Cyclobutylboronates and -silanes2.1 Diastereoselective Synthesis of Cyclopropyl- and Cyclobutylboronates and -silanes2.2 Asymmetric Synthesis of Cyclopropyl- and Cyclobutylboronates and -silanes3 Conclusions

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2

Khalil, Salim M., та Hayfa M. Jarjis. "A Theoretical Study of α-CFnH3-n -substituted Cyclopropyl Cations". Zeitschrift für Naturforschung A 45, № 5 (1990): 730–32. http://dx.doi.org/10.1515/zna-1990-0524.

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Abstract MINDO-forces calculations are performed, with complete optimization of geometries, on α-Xcyclopropylcations, where X is CF3 , CF2H, and CFH2. It was found that the fluorine atom interacts with the localized empty Pπ-type orbital on α-carbon atom and forms a bridge with an angle 57.1 degree. Calculations also are performed on CF3-cyclopropyl anion and CF2H-cyclopropenyl cation. The fluorine atom in CF3 and CF2H shows no such interaction with the a-carbon atom because there is no localized empty Prc-type orbital

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3

Časar, Zdenko. "Synthetic Approaches to Contemporary Drugs that Contain the Cyclopropyl Moiety." Synthesis 52, no. 09 (2020): 1315–45. http://dx.doi.org/10.1055/s-0039-1690058.

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The U.S. Food and Drug Administration approved 18 new drugs that incorporate the cyclopropyl structural motif in the time frame from 2012 to 2018. This review provides an overview of synthetic approaches to these drugs with emphasis on the construction of the cyclopropyl moiety or its incorporation into the key building blocks for assembly of the highlighted drugs. Based on the structural diversity of these drugs, synthetic approaches for the construction and introduction of the cyclopropyl moiety into their structure are diverse and include: cycloalkylation (double alkylation) of CH-acids, ca

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4

O'Neill, Melanie A., and Frances L. Cozens. "Influence of alkali metal cations on the photoheterolysis of 9-cyclopropyl-9-fluorenol and the reactivity of the 9-cyclopropyl-9-fluorenyl cation in non-acidic zeolites." Canadian Journal of Chemistry 81, no. 6 (2003): 647–59. http://dx.doi.org/10.1139/v03-071.

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Alkali metal cation regulation of carbocation formation and reactivity in non-acidic zeolites is probed using the photoheterolysis reaction of 9-cyclopropyl-9-fluorenol. Nanosecond time-resolved diffuse reflectance is employed to directly observe the 9-cyclopropyl-9-fluorenyl cation as a transient species within the non-acidic zeolites. The efficiency of carbocation formation via photoheterolysis and the dynamics of other reaction pathways available to photoexcited 9-cyclopropyl-9-fluorenol are found to be strongly dependent on the zeolite alkali metal counterion. In particular, the yield of c

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5

Zhang, Zhiguo, Yongchao Zhang, Guoqing Huang, and Guisheng Zhang. "Organoiodine reagent-promoted intermolecular oxidative amination: synthesis of cyclopropyl spirooxindoles." Organic Chemistry Frontiers 4, no. 7 (2017): 1372–75. http://dx.doi.org/10.1039/c7qo00156h.

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An organoiodine-promoted intramolecular direct oxidative C(sp<sup>2</sup>)–N cross-coupling reaction was developed for the preparation of cyclopropyl spirooxindoles from readily available secondary cyclopropyl carboxamides.

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6

Jeffries, Benjamin, Zhong Wang, Robert I. Troup, et al. "Lipophilicity trends upon fluorination of isopropyl, cyclopropyl and 3-oxetanyl groups." Beilstein Journal of Organic Chemistry 16 (September 2, 2020): 2141–50. http://dx.doi.org/10.3762/bjoc.16.182.

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A systematic comparison of lipophilicity modulations upon fluorination of isopropyl, cyclopropyl and 3-oxetanyl substituents, at a single carbon atom, is provided using directly comparable, and easily accessible model compounds. In addition, comparison with relevant linear chain derivatives is provided, as well as lipophilicity changes occurring upon chain extension of acyclic precursors to give cyclopropyl containing compounds. For the compounds investigated, fluorination of the isopropyl substituent led to larger lipophilicity modulation compared to fluorination of the cyclopropyl substituen

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7

Singh, Okram Mukherjee, H. Junjappa, and H. Ila. "A Facile Synthesis of 3-Cyclopropyl- and 5-Cyclopropyl-isoxazoles." Journal of Chemical Research 23, no. 6 (1999): 398–99. http://dx.doi.org/10.1177/174751989902300627.

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Ernst, Ludger, Thomas Rieck, and Mark Soliven. "Article." Canadian Journal of Chemistry 77, no. 11 (1999): 1697–706. http://dx.doi.org/10.1139/v99-130.

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Schaefer's "J method" was employed to show that 2-cyclopropyl-1,3-dimethylbenzene (5) in solution prefers the perpendicular conformation in which the torsional angle Θ between the C(1)-H bond of the cyclopropyl group and the plane of the benzene ring is 90°. This is opposed to the situation in cyclopropylbenzene (3) where the bisected conformer (Θ = 0°) prevails. From the value of -0.85 ± 0.01 Hz for 6J(H-alpha,H-para) in 5 (for solutions in CS2 and in acetone) a barrier to rotation about the cyclopropyl-aryl bond of 6.4 kJ/mol can be derived if a predominantly two-fold potential and a vanishi

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9

Redfern, Paul C., Jane S. Murray, and Peter Politzer. "Computational determination of the relative stabilities of some nitro carbocations." Canadian Journal of Chemistry 70, no. 2 (1992): 636–41. http://dx.doi.org/10.1139/v92-087.

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The relative stabilities of a group of nitro carbocations (derivatives of the methyl, cyclopropyl, and cyclopropenyl cations) are determined by means of abinitio SCF/3-21G calculations, and compared to the corresponding results for other substituent groups, both electron donating and withdrawing. The α-nitro carbocations are generally destabilized relative to the parent cation, but often to a lesser extent than anticipated from the strongly electron-withdrawing nature of NO2. The optimized structures indicate that this is due to the stabilizing formation of an intramolecular ring involving the

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10

Holland, Herbert L., Michael J. Chernishenko, Morgan Conn, Anthony Munoz, T. Samuel Manoharan, and Michael A. Zawadski. "Enzymic hydroxylation and sulfoxidation of cyclopropyl compounds by fungal biotransformation." Canadian Journal of Chemistry 68, no. 5 (1990): 696–700. http://dx.doi.org/10.1139/v90-107.

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A series of compounds containing a cyclopropyl ring adjacent to the position of oxidation during fungal biotransformation has been prepared and subjected to enzymic oxidation using Mortierellaisabellina or Rhizopusarrhizus. Carbon hydroxylation and sulfoxidation reactions were observed, but in neither case did opening of the cyclopropyl ring occur. Both these reactions were subject to inhibition by carbon monoxide but not by cyanide ion, properties characteristic of cytochrome P-450 dependent mono-oxygenase enzymes. Hydroxylation at a cyclopropyl C—H bond has been studied by the use of phenylc

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Dissertations / Theses on the topic "Cyclopropyl chemistry"

1

Shortt, Marie Fiona. "Synthetic approaches to biologically active molecules." Thesis, Bangor University, 1994. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.282267.

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2

Licisyn, Thomas A. "Synthesis of cyclopropyl glycosides and glycosyl phenylsulfinate esters applications in carbohydrate chemistry /." Click here for download, 2007. http://proquest.umi.com/pqdweb?did=1276418261&sid=2&Fmt=2&clientId=3260&RQT=309&VName=PQD.

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3

Yeats, Keith. "An investigation into the synthesis and crosslinking of some polymers containing cyclopropyl groups." Thesis, Durham University, 1990. http://etheses.dur.ac.uk/6051/.

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The thesis describes an investigation into the use of polymers containing cyclopropyl groups as network forming materials. The initial route investigated involved the synthesis and homopolymerization of novel acrylate and methacrylate monomers containing cyclopropyl groups. Preliminary crosslinking experiments revealed the unsuitability of this approach. The second route examined involved the synthesis of a series of all hydrocarbon copolymers containing pendant cyclopropyl groups. Crosslinking experiments using a variety of initiators demonstrated the feasibility, in principle, of the propose

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4

Biggs, Timothy Nolen. "Part I. Thermal and photochemical rearrangements of p-quinol cyclopropyl ethers to spiro-fused tetralones. Part II. Preparation and reactivity of p-benzoquinol imines. Investigation of glutathione/quinol imine coupling and quinol... /." The Ohio State University, 1994. http://rave.ohiolink.edu/etdc/view?acc_num=osu1487849696967873.

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5

Cui, Wenge Cui Wenge. "Part 1, Glyoxal-guanine DNA adducts, derivatization, structure, stability and new detection methodology ; Part 2, Nitrosation studies of oxazolines and imidazolines and the synthesis of N-cyclopropyl aromatic amines /." free to MU campus, to others for purchase, 2000. http://wwwlib.umi.com/cr/mo/fullcit?p9998477.

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Dufrois, Quentin. "Complexes de métaux électropositifs à travers le prisme du groupe cyclopropyle." Thesis, Toulouse 3, 2016. http://www.theses.fr/2016TOU30303/document.

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La thèse présente la chimie de complexes de métaux électropositifs portant le groupe cyclopropyle. La première partie du manuscrit décrit la synthèse et la caractérisation de dérivés du cyclopropyllithium ayant pour formule [1-R-c-C3H4Li] (R = SiMe3, Ph, SPh). Des agrégats originaux, organisés autour de centres Li+ stabilisés par la peu commune interaction CC agostique, sont présentés. Cette interaction a une influence marquée sur l'agrégation des composés à l'état solide et parfois en solution. Sa coordination compétitive, sur un Li+, avec des atomes donneurs (O, N et S) permet une évaluation

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Blunden, Ralph Benedict. "Novel early transition metal cyclopropenyl complexes." Thesis, University of Sussex, 1997. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.360552.

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Gunbas, Duygu Deniz. "Functionalization Of Saturated Hydrocarbons: High Temperature Bromination." Master's thesis, METU, 2006. http://etd.lib.metu.edu.tr/upload/2/12607307/index.pdf.

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ABSTRACT FUNCTIONALIZATION OF SATURATED HYDROCARBONS: HIGH TEMPERATURE BROMINATION G&uuml<br>nbaS, Duygu Deniz M.S., Department of Chemistry Supervisor: Prof. Dr. Metin Balci June 2006, 174 pages Although saturated hydrocarbons are readily available and extremely cheap starting materials, they can not be used in synthetic chemistry without prior activation. Efficient functionalization of alkanes leading to the production of useful organic chemicals in an industrial scale is of considerable interest for the chemical and pharmaceutical industries and remains a long-term challenge for

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9

Lowe, Kimberly Lorraine. "Mechanistic study of the 1-cyclopropyl-2,2-dimethyl-1,3-cyclopentanediyl biradical." Thesis, 1994. http://hdl.handle.net/1911/13862.

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The synthesis of the azoalkane precursor 21 was accomplished through a Diels-Alder route. This precursor provided a clean and convenient source of the 1,3-biradical 13 upon photolysis. Determination of the product ratio from the triplet biradical by gas chromatographic analysis yielded the rate of intersystem crossing of the biradical from the triplet to the singlet energy state. Structure confirmation of the cyclopropyl ring opening product was accomplished through co-injections of photolysis product and an authentic sample on two different GC columns. The lifetime of 13T was found to lie in

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Culotta, Anne Marie. "Photolysis of azoalkanes. Reactions and kinetics of the 1-cyclopropyl-1,3-cyclopentanediyl biradical and 1-cyclopropylcyclopentyl radical." Thesis, 1991. http://hdl.handle.net/1911/16434.

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The 1-cyclopropylcyclopentyl radical (114a) and 1-cyclopropylcyclohexyl radical (114b) were generated in the presence of PhSH via 366 nm photolysis of azo-1-cyclopropylcyclopentane and azo-1-cyclopropylcyclohexane respectively. These radicals undergo cyclopropylcarbinyl (CPC) rearrangement to primary homoallylic radicals 115a and 115b, respectively, at rates of 1.45 $\times$ 10$\sp7$ s$\sp{-1}$ and 1.1 $\times$ 10$\sp7$ s$\sp{-1}$ based on competitive trapping with PhSH. These rates are 6-9 times slower than the parent CPC radical. E$\sb{\rm a}$ for 114a$\to$115a was found to be 7.0 kcal/mol a

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Books on the topic "Cyclopropyl chemistry"

1

Rappoport, Zvi, ed. The Chemistry of the Cyclopropyl Group. John Wiley & Sons, Ltd, 1995. http://dx.doi.org/10.1002/0470023481.

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2

Zvi, Rappoport, ed. The chemistry of the cyclopropyl group. Wiley, 1987.

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Zvi, Rappoport, ed. The Chemistry of the cyclopropyl group. Wiley, 1995.

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Rappoport, Zvi. The Chemistry of the Cyclopropyl Group Volume 2 (Chemistry of Functional Groups). Wiley, 1996.

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5

Conti, Nicholas Joseph. Thermal and photo-induced rearrangements of sigma-bound cyclopropyl iron complexes: Synthesis of a novel metallacyclic iron dicarbene complex. 1987.

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Book chapters on the topic "Cyclopropyl chemistry"

1

Krass, Norbert, Ludger Wessjohann, Dahai Yu, and Armin Meijere. "Cyclopropyl Group Containing Amino Acids From α-Chlorocyclopropylidenacetates." In Strain and Its Implications in Organic Chemistry. Springer Netherlands, 1989. http://dx.doi.org/10.1007/978-94-009-0929-8_42.

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2

Suckling, C. J. "The Cyclopropyl Group in Studies of Enzyme-Catalysed Reactions." In Strain and Its Implications in Organic Chemistry. Springer Netherlands, 1989. http://dx.doi.org/10.1007/978-94-009-0929-8_13.

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3

Trost, Barry M. "Some Synthetic Implications of the Concept of Cyclopropyl Units as Pseudo-Functional Groups." In Strain and Its Implications in Organic Chemistry. Springer Netherlands, 1989. http://dx.doi.org/10.1007/978-94-009-0929-8_1.

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4

Tschersich, Roxanne, Carolin Bisterfeld, and Jörg Pietruszka. "Cyclopropyl Lactone-Containing Marine Oxylipins." In Studies in Natural Products Chemistry. Elsevier, 2018. http://dx.doi.org/10.1016/b978-0-444-64068-0.00005-x.

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5

Prakash, G. K. Surya, Herwig Buchholz, V. Prakash Reddy, Armin de Meijere, and George A. Olah. "1-Ferrocenyl-1-cyclopropyl Cation: The First Long-Lived Cyclopropyl Cation." In World Scientific Series in 20th Century Chemistry. World Scientific Publishing Company, 2003. http://dx.doi.org/10.1142/9789812791405_0079.

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6

Moore, Bradley S., and Heinz G. Floss. "Biosynthesis of Cyclic Fatty Acids Containing Cyclopropyl-, Cyclopentyl-, Cyclohexyl-, and Cycloheptyl-rings." In Comprehensive Natural Products Chemistry. Elsevier, 1999. http://dx.doi.org/10.1016/b978-0-08-091283-7.00002-3.

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7

Taber, Douglass F. "Metal-Mediated C–C Ring Construction: The Lei Synthesis of (−)-Huperzine Q." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0076.

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Following the Szymoniak protocol, Morwenna S. M. Pearson-Long and Philippe Bertus of the Université du Maine added (Synthesis 2015, 47, 992) the Grignard reagent 2 to the nitrile 1 to give the cyclopropyl amine 3. Chen-Guo Feng of the Shanghai Institute of Organic Chemistry prepared (Chem. Commun. 2015, 51, 8773) the cyclobutane 6 by enantioselective conjugate addition of 5 to the unsaturated ester 4. Martin Kotora of Charles University showed (Eur. J. Org. Chem. 2015, 2868) that the zirconacycle from the eneyne 7 reacted with the aldehyde 8 to give, after iodination, the alcohol 9. Xiaoming Feng of Sichuan University used (Angew. Chem. Int. Ed. 2015, 54, 1608) a scandium catalyst to effect the intramolecular Roskamp cyclization of 10 to 11. Celia Dominguez of CHDI observed (Org. Lett. 2015, 17, 1401) that the double alkylation of the ester 12 with the dibromide 13 proceeded with high diastereoselectivity, to give 14. Hirokazu Tsukamoto of Tohoku University cyclized (Chem. Commun. 2015, 51, 8027) 15 to 16 in high ee. Daniel J. Weix of the University of Rochester found (J. Am. Chem. Soc. 2015, 137, 3237) that under the influence of an enantiomerically-pure Ti catalyst, the organonickel species derived from 18 opened the prochiral epoxide 17 to give 19 in high ee. John F. Bower of the University of Bristol optimized (J. Am. Chem. Soc. 2015, 137, 463) conditions for the highly diastereoselective Rh-mediated cyclocarbonylation of 20 to 21. Margaret A. Brimble of the University of Auckland initiated (J. Org. Chem. 2015, 80, 2231) the construction of the cyclohexenone 24 by the diastereoselective addition of 23 to the unsaturated ester 22. Olivier Baslé and Marc Maduit of ENSC Rennes devised (Chem. Eur. J. 2015, 21, 993) conditions for the preparation of 26 by enantioselective conjugate addition to the cyclohexenone 25. Yoshito Kishi of Harvard University demonstrated (Tetrahedron Lett. 2015, 56, 3220) that the carbenoid generated from the epoxide 27 cyclized to 28 with high diastereoselectivity. Wenjun Tang, also of the Shanghai Institute of Organic Chemistry, developed (Angew. Chem. Int. Ed. 2015, 54, 3033) a Pd catalyst for the diastereoselective (because it is enantioselective) cyclization of 29 to 30.

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Lambert, Tristan H. "Advances in Heterocyclic Aromatic Construction." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0068.

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Rubén Vicente and Luis A. López at the University of Oviedo in Spain reported (Angew. Chem. Int. Ed. 2012, 51, 8063) the synthesis of cyclopropyl furan 2 from alkylidene 1 and styrene by way of a zinc carbene intermediate. The same substrate 1 was also converted (Angew. Chem. Int. Ed. 2012, 51, 12128) to furan 3 via catalysis with tetrahydrothiophene in the presence of benzoic acid by J. Stephen Clark at the University of Glasgow. Xue-Long Hou at the Shanghai Institute of Organic Chemistry discovered (Org. Lett. 2012, 14, 5756) that palladacycle 6 catalyzes the conversion of bicyclic alkene 4 and alkynone 5 to furan 7. A silver-mediated C–H/C–H functionalization strategy for the synthesis of furan 9 from alkyne 8 and ethyl acetoacetate was developed (J. Am. Chem. Soc. 2012, 134, 5766) by Aiwen Lei at Wuhan University. Ning Jiao at Peking University and East China Normal University found (Org. Lett. 2012, 14, 4926) that azide 10 and aldehyde 11 could be converted to either pyrrole 12 or 13 with complete regiocontrol by judicious choice of a metal catalyst. Meanwhile, Michael A. Kerr at the University of Western Ontario developed (Angew. Chem. Int. Ed. 2012, 51, 11088) a multicomponent synthesis of pyrrole 16 involving the merger of nitrone 14 and the donor–acceptor cyclopropane 15. The pyrrole 16 was subsequently converted to an intermediate in the synthesis of the cholesterol-lowering drug compound Lipitor. A robust synthesis of the ynone trifluoroboronate 17 was developed (Org. Lett. 2012, 14, 5354) by James D. Kirkham and Joseph P.A. Harrity at the University of Sheffield, which thus allowed for the ready production of trifluoroboronate-substituted pyrazole 18. An alternative pyrazole synthesis via oxidative closure of unsaturated hydrazine 19 to produce 20 was reported (Org. Lett. 2012, 14, 5030) by Yu Rao at Tsinghua University. A unique fluoropyrazole construction was developed (Angew. Chem. Int. Ed. 2012, 51, 12059) by Junji Ichikawa at the University of Tsukuba that involved nucleophilic substitution of two of the fluorides in 21 to form pyrazole 22.

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Taber, Douglass F. "Organocatalyzed C–C Ring Construction: The Jørgenson Synthesis of (+)-Estrone." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0070.

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Ana Maria Faísca Phillips and Maria Teresa Barros of the Universidade Nova de Lisboa added (Eur. J. Org. Chem. 2014, 152) the bromo ester 1 to cinnamaldehyde 2 to give the cyclopropyl phosphonate 3 in high ee. Mukund P. Sibi and Jayaraman Sivaguru of North Dakota State University used (Angew. Chem. Int. Ed. 2014, 53, 5604) an organocatalyst to mediate the 2+2 photocycloaddition of 4, leading to 5. Shu-Li You of the Shanghai Institute of Organic Chemistry expanded (Org. Lett. 2014, 16, 1810) the four-membered ring of 6 to create the cyclopentanone 7 in high ee. Damien Bonne and Jean Rodriguez of Aix-Marseille Université condensed (Chem. Eur. J. 2014, 20, 410) the cyclopentanone 8 with 9 to give 10. Santanu Mukherjee of the Indian Institute of Science, Bangalore added (Chem. Sci. 2014, 5, 1627) the lactone 12 to the prochiral 11 to give 13 with remarkable diastereo- and enantiocontrol. Yixin Lu of the National University of Singapore constructed (Angew. Chem. Int. Ed. 2014, 53, 5643) the cyclopentene 16 by adding 14 to the allene 15. Efraim Reyes and Jose L. Vicario of the Universidad del País Vasco prepared (Chem. Eur. J. 2014, 20, 2145) the highly substituted cyclohexene 19 by combining 17 and 18. Maurizio Benaglia of the Università degli Studi di Milano added (Adv. Synth Catal. 2014, 356, 493) the ketone 20 to 21 to create the cyclohexanone 22. Ben W. Greatrex of the University of New England in Australia used (J. Org. Chem. 2014, 79, 5088) an organocatalyst to cyclize the symmetrical dialdehyde 23 to the α-hydroxy ketone 24. Dieter Enders of RWTH Aachen added (Org. Lett. 2014, 16, 2954) the β-keto ester 25 to 26 to give an intermediate that was further condensed with 27 to complete the preparation of 28. Eric N. Jacobsen of Harvard University prepared (Angew. Chem. Int. Ed. 2014, 53, 5912) the cycloheptenone 30 by the enantioselective intermolecular addition of the pyrylium salt derived from 29 to ethyl vinyl ether. Bor-Cherng Hong of the National Chung Cheng University initiated (Org. Lett. 2014, 16, 2724) the assembly of the steroid derivative 33 by the enantioselective addition of 32 to the unsaturated aldehyde 31.

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Conference papers on the topic "Cyclopropyl chemistry"

1

Marini, Francesca, Luca Rossi, Luca Sancineto, Luana Bagnoli, and Claudio Santi. "Michael Initiated Ring Closure Reactions in Aqueous Medium for the Synthesis of Spiro Cyclopropyl Oxindoles." In The 18th International Electronic Conference on Synthetic Organic Chemistry. MDPI, 2014. http://dx.doi.org/10.3390/ecsoc-18-a020.

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Ramazanov, Ilfir, Alsu Yaroslavova, Artur Kamalov, Usein Dzhemilev, and Oleg Nefedov. "Aluminum Carbenoid R₂AlCH₂I – a New Cyclopropanation Agent for the Transformation of Unsaturated Amines into Cyclopropyl Amines." In The 16th International Electronic Conference on Synthetic Organic Chemistry. MDPI, 2012. http://dx.doi.org/10.3390/ecsoc-16-01081.

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