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Published: 25 May 2024

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1

Craig, Alexander J., and Bill C. Hawkins. "The Bonding and Reactivity of α-Carbonyl Cyclopropanes." Synthesis 52, no. 01 (October 1, 2019): 27–39. http://dx.doi.org/10.1055/s-0039-1690695.

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The cyclopropane functionality has been exploited in a myriad of settings that range from total synthesis and methodological chemistry, to medical and materials science. While it has been seen in such a breadth of settings, the typical view of the cyclopropane moiety is that its reactivity is derived primarily from the release of ring strain. While this simplified view is a useful shorthand, it ignores the specific nature of cyclopropyl molecular orbitals. This review aims to present the different facets of cyclopropane bonding by examining the main models that have been used to explain the reactivity of the functionality over the years. However, even with advanced theory, being able to precisely predict the reactivity of an exact system is nigh impossible. Specifically chosen, carbonyl-bearing cyclopropyl species act as so-called acceptor cyclopropanes and, if correctly derivatised, donor–acceptor cyclopropanes. By undertaking a case study of the history of carbonyl cyclopropanes in organic synthesis, this review highlights the relationship between the understanding of theory and pattern recognition in developing new synthetic methods and showcases those successful in balancing this critical junction.1 Cyclopropanes2 The Strain Model3 The Forster–Coulsin–Moffit Model4 The Walsh Model5 Acceptor, Donor, and Donor–Acceptor Cyclopropanes6 Reactions of Carbonyl Cyclopropanes
2

Boichenko, Maksim A., Andrey Yu Plodukhin, Vitaly V. Shorokhov, Danyla S. Lebedev, Anastasya V. Filippova, Sergey S. Zhokhov, Elena A. Tarasenko, Victor B. Rybakov, Igor V. Trushkov, and Olga A. Ivanova. "Synthesis of 1,5-Substituted Pyrrolidin-2-ones from Donor–Acceptor Cyclopropanes and Anilines/Benzylamines." Molecules 27, no. 23 (December 2, 2022): 8468. http://dx.doi.org/10.3390/molecules27238468.

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We developed a straightforward synthetic route to pharmacologically important 1,5-substituted pyrrolidin-2-ones from donor–acceptor cyclopropanes bearing an ester group as one of the acceptor substituents. This method includes a Lewis acid-catalyzed opening of the donor–acceptor cyclopropane with primary amines (anilines, benzylamines, etc.) to γ-amino esters, followed by in situ lactamization and dealkoxycarbonylation. The reaction has a broad scope of applicability; a variety of substituted anilines, benzylamines, and other primary amines as well as a wide range of donor–acceptor cyclopropanes bearing (hetero)aromatic or alkenyl donor groups and various acceptor substituents can be involved in this transformation. In this process, donor–acceptor cyclopropanes react as 1,4-C,C-dielectrophiles, and amines react as 1,1-dinucleophiles. The resulting di- and trisubstituted pyrrolidin-2-ones can be also used in subsequent chemistry to obtain various nitrogen-containing polycyclic compounds of interest to medicinal chemistry and pharmacology, such as benz[g]indolizidine derivatives.
3

Mead, Keith, and Yahaira Reyes. "Acetoxy-Substituted Cyclopropane Dicarbonyls as Stable Donor–Acceptor–Acceptor Cyclopropanes." Synthesis 47, no. 19 (June 25, 2015): 3020–26. http://dx.doi.org/10.1055/s-0034-1379934.

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4

Fadeev, Alexander A., Alexey O. Chagarovskiy, Anton S. Makarov, Irina I. Levina, Olga A. Ivanova, Maxim G. Uchuskin, and Igor V. Trushkov. "Synthesis of (Het)aryl 2-(2-hydroxyaryl)cyclopropyl Ketones." Molecules 25, no. 23 (December 5, 2020): 5748. http://dx.doi.org/10.3390/molecules25235748.

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A simple general method for the synthesis of 1-acyl-2-(ortho-hydroxyaryl)cyclopropanes, which belong to the donor–acceptor cyclopropane family, has been developed. This method, based on the Corey–Chaykovsky cyclopropanation of 2-hydroxychalcones, allows for the preparation of a large diversity of hydroxy-substituted cyclopropanes, which can serve as promising building blocks for the synthesis of various bioactive compounds.
5

Grover, Huck K., Michael R. Emmett, and Michael A. Kerr. "Carbocycles from donor–acceptor cyclopropanes." Organic & Biomolecular Chemistry 13, no. 3 (2015): 655–71. http://dx.doi.org/10.1039/c4ob02117g.

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6

Reyes, Yahaira, and Keith T. Mead. "ChemInform Abstract: Acetoxy-Substituted Cyclopropane Dicarbonyls as Stable Donor-Acceptor-Acceptor Cyclopropanes." ChemInform 47, no. 7 (January 2016): no. http://dx.doi.org/10.1002/chin.201607087.

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7

Budynina, Ekaterina, Konstantin Ivanov, Ivan Sorokin, and Mikhail Melnikov. "Ring Opening of Donor–Acceptor Cyclopropanes with N-Nucleo­philes." Synthesis 49, no. 14 (May 18, 2017): 3035–68. http://dx.doi.org/10.1055/s-0036-1589021.

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Ring opening of donor–acceptor cyclopropanes with various N-nucleophiles provides a simple approach to 1,3-functionalized compounds that are useful building blocks in organic synthesis, especially in assembling various N-heterocycles, including natural products. In this review, ring-opening reactions of donor–acceptor cyclopropanes with amines, amides, hydrazines, N-heterocycles, nitriles, and the azide ion are summarized.1 Introduction2 Ring Opening with Amines3 Ring Opening with Amines Accompanied by Secondary Processes Involving the N-Center3.1 Reactions of Cyclopropane-1,1-diesters with Primary and Secondary Amines3.1.1 Synthesis of γ-Lactams3.1.2 Synthesis of Pyrroloisoxazolidines and -pyrazolidines3.1.3 Synthesis of Piperidines3.1.4 Synthesis of Azetidine and Quinoline Derivatives3.2 Reactions of Ketocyclopropanes with Primary Amines: Synthesis of Pyrrole Derivatives3.3 Reactions of Сyclopropane-1,1-dicarbonitriles with Primary Amines: Synthesis of Pyrrole Derivatives4 Ring Opening with Tertiary Aliphatic Amines5 Ring Opening with Amides6 Ring Opening with Hydrazines7 Ring Opening with N-Heteroaromatic Compounds7.1 Ring Opening with Pyridines7.2 Ring Opening with Indoles7.3 Ring Opening with Di- and Triazoles7.4 Ring Opening with Pyrimidines8 Ring Opening with Nitriles (Ritter Reaction)9 Ring Opening with the Azide Ion10 Summary
8

Ivanova, Olga, Vladimir Andronov, Irina Levina, Alexey Chagarovskiy, Leonid Voskressensky, and Igor Trushkov. "Convenient Synthesis of Functionalized Cyclopropa[c]coumarin-1a-carboxylates." Molecules 24, no. 1 (December 24, 2018): 57. http://dx.doi.org/10.3390/molecules24010057.

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A simple method has been developed for the synthesis of cyclopropa[c]coumarins, which belong to the donor-acceptor cyclopropane family and, therefore, are promising substrates for the preparation of chromene-based fine chemicals. The method, based on the acetic acid-induced intramolecular transesterification of 2-arylcyclopropane-1,1-dicarboxylates, was found to be efficient for substrates containing hydroxy group directly attached to the aromatic ring.
9

Liu, Haidong, Lifang Tian, Hui Wang, Zhi-Qiang Li, Chi Zhang, Fei Xue, and Chao Feng. "A novel type of donor–acceptor cyclopropane with fluorine as the donor: (3 + 2)-cycloadditions with carbonyls." Chemical Science 13, no. 9 (2022): 2686–91. http://dx.doi.org/10.1039/d2sc00302c.

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A new type of donor–acceptor cyclopropane with gem-difluorine as an unconventional donor group undergoes (3 + 2)-cycloadditions with various aldehydes/ketones, affording densely functionalized gem-difluorotetrahydrofurans.
10

Cavitt, Marchello A., Lien H. Phun, and Stefan France. "Intramolecular donor–acceptor cyclopropane ring-opening cyclizations." Chem. Soc. Rev. 43, no. 3 (2014): 804–18. http://dx.doi.org/10.1039/c3cs60238a.

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11

Ivanova, Olga A., Vitaly V. Shorokhov, Ivan A. Andreev, Nina K. Ratmanova, Victor B. Rybakov, Elena D. Strel’tsova, and Igor V. Trushkov. "Synthesis of 2-[2-(Ethoxymethoxy)phenyl]spiro[cyclopropane-1,2′-indene]-1′,3′-dione." Molbank 2023, no. 1 (March 14, 2023): M1604. http://dx.doi.org/10.3390/m1604.

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An 1,3-indanedione-derived donor–acceptor cyclopropane, bearing the ethoxymethyl-protected phenolic group at the ortho-position of the donor aryl substituent, has been synthesized using a reaction sequence involving the Knoevenagel condensation of 1,3-indanedione with the corresponding protected salicylaldehyde followed by the Corey–Chaykovsky cyclopropanation of the obtained adduct with dimethylsulfoxonium methylide. The structure of the synthesized cyclopropane was unambiguously proved by single-crystal X-ray diffraction data.
12

Mlostoń, Grzegorz, Mateusz Kowalczyk, André U. Augustin, Peter G. Jones, and Daniel B. Werz. "Ferrocenyl-substituted tetrahydrothiophenes via formal [3 + 2]-cycloaddition reactions of ferrocenyl thioketones with donor–acceptor cyclopropanes." Beilstein Journal of Organic Chemistry 16 (June 10, 2020): 1288–95. http://dx.doi.org/10.3762/bjoc.16.109.

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Ferrocenyl thioketones reacted with donor–acceptor cyclopropanes in dichloromethane at room temperature in the presence of catalytic amounts of Sc(OTf)3 yielding tetrahydrothiophene derivatives, products of formal [3 + 2]-cycloaddition reactions, in moderate to high yields. In all studied cases, dimethyl 2-arylcyclopropane dicarboxylates reacted with the corresponding aryl ferrocenyl thioketones in a completely diastereoselective manner to form single products in which (C-2)-Ar and (C-5)-ferrocenyl groups were oriented in a cis-fashion. In contrast, the same cyclopropanes underwent reaction with alkyl ferrocenyl thioketones to form nearly equal amounts of both diastereoisomeric tetrahydrothiophenes. A low selectivity was also observed in the reaction of a 2-phthalimide-derived cyclopropane with ferrocenyl phenyl thioketone.
13

Hayakawa, Kosuke, Shin-ichi Matsuoka, and Masato Suzuki. "Ring-opening polymerization of donor–acceptor cyclopropanes catalyzed by Lewis acids." Polymer Chemistry 8, no. 25 (2017): 3841–47. http://dx.doi.org/10.1039/c7py00794a.

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14

Augustin, André U., and Daniel B. Werz. "Exploiting Heavier Organochalcogen Compounds in Donor–Acceptor Cyclopropane Chemistry." Accounts of Chemical Research 54, no. 6 (March 4, 2021): 1528–41. http://dx.doi.org/10.1021/acs.accounts.1c00023.

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15

Cavitt, Marchello A., Lien H. Phun, and Stefan France. "ChemInform Abstract: Intramolecular Donor-Acceptor Cyclopropane Ring-Opening Cyclizations." ChemInform 45, no. 17 (April 10, 2014): no. http://dx.doi.org/10.1002/chin.201417267.

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16

Kreft, Alexander, Peter G. Jones, and Daniel B. Werz. "The Cyclopropyl Group as a Neglected Donor in Donor–Acceptor Cyclopropane Chemistry." Organic Letters 20, no. 7 (March 20, 2018): 2059–62. http://dx.doi.org/10.1021/acs.orglett.8b00603.

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17

Sliwinska, Anna, Wojciech Czardybon, and John Warkentin. "Zwitterion from a Cyclopropane with Geminal Donor and Acceptor Groups." Organic Letters 9, no. 4 (February 2007): 695–98. http://dx.doi.org/10.1021/ol063021s.

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18

Alonso, Miguel E., Sarah V. Pekerar, and Maria L. Borgo. "Transmission of electronic effects through 2-[donor]-1-[acceptor]-cyclopropane." Magnetic Resonance in Chemistry 28, no. 11 (November 1990): 956–62. http://dx.doi.org/10.1002/mrc.1260281110.

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19

Cruz-Cabeza, Aurora J., and Frank H. Allen. "Geometry and conformation of cyclopropane derivatives having σ-acceptor and σ-donor substituents: a theoretical and crystal structure database study." Acta Crystallographica Section B Structural Science 68, no. 2 (February 25, 2012): 182–88. http://dx.doi.org/10.1107/s0108768111054991.

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The structures of cyclopropane rings which carry σ-acceptor or σ-donor substituents have been studied using density-functional theory (DFT), and mean bond lengths and conformational parameters retrieved from the Cambridge Structural Database. It is confirmed that σ-acceptor substituents, e.g. halogens, generate positive ring bond-length asymmetry in which there is lengthening of the distal bond (opposite to the point of substitution), and shortening of the two vicinal bonds. This is due to withdrawal of electron density from the cyclopropane 1e′′ orbitals, which are bonding for the distal bond and antibonding for the vicinal bonds. For σ-donor substituents such as SiH3 or Si(CH3)3, the DFT and crystal structure data show negative ring bond-length asymmetry (distal bond shortened, vicinal bonds lengthened), owing to electron donation into the 4e′ ring orbital, which are also bonding for the distal bond and antibonding for the vicinal bonds. The results also show that —OH substituents induce weak positive asymmetry, but that the effects of methyl or amino substituents are either non-existent or extremely small, certainly too small to measure using crystal structure information.
20

Allen, F. H., J. P. M. Lommerse, V. J. Hoy, J. A. K. Howard, and G. R. Desiraju. "The hydrogen-bond C–H donor and π-acceptor characteristics of three-membered rings." Acta Crystallographica Section B Structural Science 52, no. 4 (August 1, 1996): 734–45. http://dx.doi.org/10.1107/s0108768196005319.

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Crystallographic results, retrieved from the Cambridge Structural Database, show that the C--H protons of cyclopropane, aziridine and oxirane form C—H...O (particularly C—H...O—C) hydrogen bonds. The frequency of formation and geometrical characteristics of these bonds indicate a bond-strength ordering: Csp 1—H...O > C(ring)—H...O ≃ Csp 2—H...O > Csp 3—H...O, which is in excellent agreement with the well known ethylenic properties of C(ring)—H and with residual δ+ charges calculated for these systems. There is some evidence to suggest that C=C—H in cyclopropene, known to be a highly acidic H, forms stronger hydrogen bonds than C—H in saturated three-membered rings. Crystallographic data have also been used to provide geometrical evidence for the formation of O,N—H...π(ring) bonding to three-membered rings, proposed on the basis of spectroscopic data [Joris, Schleyer & Gleiter (1968). J. Am. Chem. Soc. 90, 327–336]. The two modes of H...π(ring) binding suggested there, viz. `edge-on' approach of H to a ring C—C bond and `face-on' approach towards the ring centroid, are found to be dominant in crystallographic observations of this novel hydrogen bond.
21

Reissig, Hans-Ulrich, and Reinhold Zimmer. "Donor−Acceptor-Substituted Cyclopropane Derivatives and Their Application in Organic Synthesis†." Chemical Reviews 103, no. 4 (April 2003): 1151–96. http://dx.doi.org/10.1021/cr010016n.

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22

Beyzavi, M. Hassan, Carolin Nietzold, Hans-Ulrich Reissig, and Arno Wiehe. "Synthesis of Functionalizedtrans-A2B2-Porphyrins Using Donor-Acceptor Cyclopropane-Derived Dipyrromethanes." Advanced Synthesis & Catalysis 355, no. 7 (April 30, 2013): 1409–22. http://dx.doi.org/10.1002/adsc.201300141.

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23

Zhang, Yanqun, Manyu Jin, Cunqi Wu, Yongxia Zhao, Hua Zhou, and Jingwei Xu. "A practical and reusable catalyst for the synthesis of donor-acceptor cyclopropane." Catalysis Communications 103 (January 2018): 5–9. http://dx.doi.org/10.1016/j.catcom.2017.09.009.

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24

Levitskiy, Oleg A., Olga I. Aglamazova, Yuri K. Grishin, and Tatiana V. Magdesieva. "Reductive opening of a cyclopropane ring in the Ni(II) coordination environment: a route to functionalized dehydroalanine and cysteine derivatives." Beilstein Journal of Organic Chemistry 18 (September 8, 2022): 1166–76. http://dx.doi.org/10.3762/bjoc.18.121.

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The involvement of an α,α-cyclopropanated amino acid in the chiral Ni(II) coordination environment in the form of a Schiff base is considered as a route to electrochemical broadening of the donor–acceptor cyclopropane concept in combination with chirality induction in the targeted products. A tendency to the reductive ring-opening and the follow-up reaction paths of thus formed radical anions influenced by substituents in the cyclopropane ring are discussed. Optimization of the reaction conditions opens a route to the non-proteinogenic amino acid derivatives containing an α–β or β–γ double C=C bond in the side chain; the regioselectivity can be tuned by the addition of Lewis acids. One-pot combination of the reductive ring opening and subsequent addition of thiols allows obtaining the cysteine derivatives in practical yields and with high stereoselectivity at the removed β-stereocenter.
25

Morales, Christian L., and Brian L. Pagenkopf. "Total Synthesis of (±)-Goniomitine via a Formal Nitrile/Donor−Acceptor Cyclopropane [3 + 2] Cyclization." Organic Letters 10, no. 2 (January 2008): 157–59. http://dx.doi.org/10.1021/ol702376j.

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26

Zheng, Xiaomei, and Michael A. Kerr. "Synthesis and Cross-Coupling Reactions of 7-Azaindoles via a New Donor−Acceptor Cyclopropane." Organic Letters 8, no. 17 (August 2006): 3777–79. http://dx.doi.org/10.1021/ol061379i.

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27

Brand, Christian, Gesche Rauch, Michele Zanoni, Birger Dittrich, and Daniel B. Werz. "Synthesis of [n,5]-Spiroketals by Ring Enlargement of Donor-Acceptor-Substituted Cyclopropane Derivatives." Journal of Organic Chemistry 74, no. 22 (November 20, 2009): 8779–86. http://dx.doi.org/10.1021/jo901902g.

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28

Beyzavi, M. Hassan, Carolin Nietzold, Hans-Ulrich Reissig, and Arno Wiehe. "ChemInform Abstract: Synthesis of Functionalized trans-A2B2-Porphyrins Using Donor-Acceptor Cyclopropane-Derived Dipyrromethanes." ChemInform 44, no. 38 (August 30, 2013): no. http://dx.doi.org/10.1002/chin.201338109.

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29

Sabbatani, Juliette, and Nuno Maulide. "Temporary Generation of a Cyclopropyl Oxocarbenium Ion Enables Highly Diastereoselective Donor-Acceptor Cyclopropane Cycloaddition." Angewandte Chemie International Edition 55, no. 23 (April 21, 2016): 6780–83. http://dx.doi.org/10.1002/anie.201601340.

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30

Kang, Qikai, Lijia Wang, Zhongbo Zheng, Junfang Li, and Yong Tang. "Sidearm as a Control in the Asymmetric Ring Opening Reaction of Donor-Acceptor Cyclopropane." Chinese Journal of Chemistry 32, no. 8 (April 4, 2014): 669–72. http://dx.doi.org/10.1002/cjoc.201400053.

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31

Lund, Elizabeth A., Isaac A. Kennedy, and Alex G. Fallis. "Dihydrofurans from α-diazoketones due to facile ring opening – cyclization of donor–acceptor cyclopropane intermediates." Canadian Journal of Chemistry 74, no. 12 (December 1, 1996): 2401–12. http://dx.doi.org/10.1139/v96-269.

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A series of α-diazoketones, 8, 25, 28, 31, and 34, have been synthesized and their reaction with ethyl vinyl ether examined under various reaction conditions. In the presence of metal salts (Rh2(OAc)4, Pd(OAc)2, CuCl) the ethoxy-dihydrofurans 12, 37, 39, 41, and 43 are produced. Sensitized irradiation of the α-diazoketone 8 afforded the dihydrofuran 12 plus cyclobutanone 7, while direct photolysis of α-diazoketones 8, 25, 28, 31, and 34 gave the cyclobutanones 7, 38,40,42, and 44, respectively. A sample of the cyclopropylketone 45 was isolated from the rhodium(II) acetate mediated reaction of 34 and its facile rearrangement to dihydrofuran 43 demonstrated. Collectively, these results indicate that the initial product from the reaction of an α-diazoketone with an electron-rich alkene such as ethyl vinyl ether is a cyclopropylketone. The donnor–acceptor substitution pattern of this intermediate results in spontaneous rearrangement to a dihydrofuran. Thus a direct dipolar cycloaddition mechanism is not involved when α-diazoketones react with enol ethers under metal-mediated conditions. Instead, these reactions follow a cyclopropanation rearrangement or, more accurately, cyclopropanation – ring opening – cyciization pathway. Key words: diazoketone, rhodium acetate, dihydrofuran, cyclopropylketone, vinyl ether.
32

Pilsl, Ludwig K. A., Thomas Ertl, and Oliver Reiser. "Enantioselective Three-Step Synthesis of Homo-β-proline: A Donor–Acceptor Cyclopropane as Key Intermediate." Organic Letters 19, no. 10 (May 9, 2017): 2754–57. http://dx.doi.org/10.1021/acs.orglett.7b01111.

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33

Gharpure, Santosh J., Laxmi Narayan Nanda, and Dimple Kumari. "Enantiospecific Total Synthesis of (+)-3-epi -Epohelmin A Using a Nitrogen-Substituted Donor-Acceptor Cyclopropane." European Journal of Organic Chemistry 2017, no. 27 (July 18, 2017): 3917–20. http://dx.doi.org/10.1002/ejoc.201700498.

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34

Alford, Joshua S., and Huw M. L. Davies. "Expanding the Scope of Donor/Acceptor Carbenes to N-Phthalimido Donor Groups: Diastereoselective Synthesis of 1-Cyclopropane α-Amino Acids." Organic Letters 14, no. 23 (November 15, 2012): 6020–23. http://dx.doi.org/10.1021/ol3029127.

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35

Gharpure, Santosh J., Laxmi Narayan Nanda, and Manoj Kumar Shukla. "Donor–Acceptor Substituted Cyclopropane to Butanolide and Butenolide Natural Products: Enantiospecific First Total Synthesis of (+)-Hydroxyancepsenolide." Organic Letters 16, no. 24 (December 8, 2014): 6424–27. http://dx.doi.org/10.1021/ol503246k.

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36

Novikov, Roman A., Anna V. Tarasova, Victor A. Korolev, Vladimir P. Timofeev, and Yury V. Tomilov. "A New Type of Donor-Acceptor Cyclopropane Reactivity: The Generation of Formal 1,2- and 1,4-Dipoles." Angewandte Chemie 126, no. 12 (February 19, 2014): 3251–55. http://dx.doi.org/10.1002/ange.201306186.

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37

Kang, Qikai, Lijia Wang, Zhongbo Zheng, Junfang Li, and Yong Tang. "ChemInform Abstract: Sidearm as a Control in the Asymmetric Ring Opening Reaction of Donor-Acceptor Cyclopropane." ChemInform 46, no. 8 (February 2015): no. http://dx.doi.org/10.1002/chin.201508033.

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38

Novikov, Roman A., Anna V. Tarasova, Victor A. Korolev, Vladimir P. Timofeev, and Yury V. Tomilov. "A New Type of Donor-Acceptor Cyclopropane Reactivity: The Generation of Formal 1,2- and 1,4-Dipoles." Angewandte Chemie International Edition 53, no. 12 (February 19, 2014): 3187–91. http://dx.doi.org/10.1002/anie.201306186.

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39

Alonso, Miguel E., and Sarah V. Pekerar. "Transmission of electronic effects through cyclopropane. II.—Comparative modulation of1H chemical shifts by aryloxy and aryl substituents in 2-(donor)-1-(acceptor)cyclopropanes." Magnetic Resonance in Chemistry 29, no. 6 (June 1991): 587–93. http://dx.doi.org/10.1002/mrc.1260290609.

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40

Xiao, Jun-An, Jie Li, Peng-Ju Xia, Zhao-Fang Zhou, Zhao-Xu Deng, Hao-Yue Xiang, Xiao-Qing Chen, and Hua Yang. "Diastereoselective Intramolecular [3 + 2]-Annulation of Donor–Acceptor Cyclopropane with Imine-Assembling Hexahydropyrrolo[3,2-c]quinolinone Scaffolds." Journal of Organic Chemistry 81, no. 22 (November 3, 2016): 11185–94. http://dx.doi.org/10.1021/acs.joc.6b02172.

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41

LUND, E. A., I. A. KENNEDY, and A. G. FALLIS. "ChemInform Abstract: Dihydrofurans from α-Diazoketones Due to Facile Ring Opening - Cyclization of Donor-Acceptor Cyclopropane Intermediates." ChemInform 28, no. 27 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199727124.

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42

Alford, Joshua S., and Huw M. L. Davies. "ChemInform Abstract: Expanding the Scope of Donor/Acceptor Carbenes to N-Phthalimido Donor Groups: Diastereoselective Synthesis of 1-Cyclopropane α-Amino Acids." ChemInform 44, no. 19 (April 18, 2013): no. http://dx.doi.org/10.1002/chin.201319048.

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43

Ghosh, Asit, Subhajit Mandal, Pratim Kumar Chattaraj, and Prabal Banerjee. "Ring Expansion of Donor–Acceptor Cyclopropane via Substituent Controlled Selective N-Transfer of Oxaziridine: Synthetic and Mechanistic Insights." Organic Letters 18, no. 19 (September 29, 2016): 4940–43. http://dx.doi.org/10.1021/acs.orglett.6b02417.

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44

Novikov, Roman A., Anna V. Tarasova, Victor A. Korolev, Vladimir P. Timofeev, and Yury V. Tomilov. "ChemInform Abstract: A New Type of Donor-Acceptor Cyclopropane Reactivity: The Generation of Formal 1,2- and 1,4-Dipoles." ChemInform 45, no. 36 (August 21, 2014): no. http://dx.doi.org/10.1002/chin.201436034.

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45

Vartanova, Anna E., Irina I. Levina, Victor B. Rybakov, Olga A. Ivanova, and Igor V. Trushkov. "Donor–Acceptor Cyclopropane Ring Opening with 6-Amino-1,3-dimethyluracil and Its Use in Pyrimido[4,5-b]azepines Synthesis." Journal of Organic Chemistry 86, no. 17 (August 12, 2021): 12300–12308. http://dx.doi.org/10.1021/acs.joc.1c01064.

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46

Yang, Hua, Jie Li, Jun-An Xiao, Shu-Juan Zhao, and Hao-Yue Xiang. "Facile Construction of Pyrrolo[1,2-a]indolenine Scaffold via Dia­stereoselective [3+2] Annulation of Donor–Acceptor Cyclopropane with Indolenine." Synthesis 49, no. 18 (July 19, 2017): 4292–98. http://dx.doi.org/10.1055/s-0036-1588876.

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Abstract:
A novel synthetic protocol for the assembly of pyrrolo[1,2-a]indolenine has been developed through a highly diastereoselective [3+2] annulation of 1,1-cyclopropanediesters with indolenines in the presence of catalytic Yb(OTf)3. This new strategy allows a facile construction of the multicyclic system with the flexible variation on the substituents in high yields (up to 86%) with excellent diastereoselectivities (>20:1 dr) in most cases.
47

Maslivetc, Vladimir A., Marina Rubina, and Michael Rubin. "One-pot synthesis of GABA amides via the nucleophilic addition of amines to 3,3-disubstituted cyclopropenes." Organic & Biomolecular Chemistry 13, no. 34 (2015): 8993–95. http://dx.doi.org/10.1039/c5ob01462j.

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Abstract:
A one-pot synthesis of various GABA amides has been demostrated, employing the nucleophilic addition of primary and secondary amines across the double bond of cyclopropene-3-carboxamides, followed by ring-opening of the resulting donor–acceptor cyclopropanes and subsequent in situ reduction of enamine intermediates.
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Alonso, Miguel E., José Daniel Gómez, and Sarah V. Pekerar. "Transmission of electronic effects through 2-[donor]-1-[acceptor] cyclopropanes. Part III. Conformational studies of 2-(p-x-aryl)-1-cyclopropane aldehydes with lanthanide shift reagents." Tetrahedron 49, no. 34 (August 1993): 7427–36. http://dx.doi.org/10.1016/s0040-4020(01)87219-7.

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49

Sundaravelu, Nallappan, and Govindasamy Sekar. "Domino Synthesis of Thioflavones and Thioflavothiones by Regioselective Ring Opening of Donor–Acceptor Cyclopropane Using In-Situ-Generated Thiolate Anions." Organic Letters 21, no. 17 (August 16, 2019): 6648–52. http://dx.doi.org/10.1021/acs.orglett.9b02210.

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50

Zheng, Zhong‐Bo, Wen‐Fu Cheng, Lijia Wang, Jun Zhu, Xiu‐Li Sun, and Yong Tang. "Asymmetric Catalytic [3+2] Annulation of Donor‐Acceptor Cyclopropane with Cyclic Ketones: Facile Access to Enantioenriched 1‐Oxaspiro [4.5]decanes †." Chinese Journal of Chemistry 38, no. 12 (October 6, 2020): 1629–34. http://dx.doi.org/10.1002/cjoc.202000277.

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