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Journal articles on the topic 'Synthesis of cyclopropanes'

Author: Grafiati

Published: 4 June 2021

Last updated: 14 February 2022

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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

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2

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.

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3

Fang, Zeguo, Nawaf Al-Maharik, Peer Kirsch, Matthias Bremer, Alexandra M. Z. Slawin, and David O’Hagan. "Synthesis of organic liquid crystals containing selectively fluorinated cyclopropanes." Beilstein Journal of Organic Chemistry 16 (April 14, 2020): 674–80. http://dx.doi.org/10.3762/bjoc.16.65.

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This paper describes the synthesis of a series of organic liquid crystals (LCs) containing selectively fluorinated cyclopropanes at their termini. The syntheses used difluorocarbene additions to olefin precursors, an approach which proved straightforward such that these liquid crystal candidates could be efficiently prepared. Their physical and thermodynamic properties were evaluated and depending on individual structures, they either displayed positive or negative dielectric anisotropy. The study gives some guidance into effective structure–property relationships for the design of LCs containing selectively fluorinated cyclopropane motifs.

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4

Ben Hamadi, Naoufel, Ahlem Guesmi, and Wided Nouira. "Asymmetric one-pot synthesis of cyclopropanes." Macedonian Journal of Chemistry and Chemical Engineering 35, no. 1 (April 18, 2016): 45. http://dx.doi.org/10.20450/mjcce.2016.835.

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Cycloaddition of the diazoalkanes to electron-deficient olefins (in situ) affords polysubstituted cyclopropanes in high yields (up to 85%). Deprotection of the ketal protecting group provided water-soluble cyclopropane-bearing carbohydrate in good yields. Antimicrobial activity screening of the synthesized compounds 8 and 9, utilizing a variety of Gram-positive (Staphylococcus aureus and Enterococcus fecalis), Gram-negative bacteria (Escherichia coli and Klebsiella pneumoniae) and yeast (Candida albicans), exhibited that all the prepared analogues acquire promising activities against both Gram-positive and Gram-negative bacteria especially compounds 9b and 9c (antimicrobial active agents against Gram-negative bacteria).

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5

Finta, Zoltán, Zoltán Hell, Agnieszka Cwik, and László Tőke. "A Simple Synthesis of 1,1,2-tris-(Hydroxymethyl)-Cyclopropane and Its Dihalo Derivatives." Journal of Chemical Research 2002, no. 9 (September 2002): 459–60. http://dx.doi.org/10.3184/030823402103172653.

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The phase transfer catalytic cyclopropanation of the malonic ester of allylic alcohol or its 3,3-dibromo and 3,3-dichloro derivatives yields bicyclic cyclopropane carboxylic acid lactones; reduction of these lactones with LiAlH4 in boiling THF yields the appropriate 1,1,2-tris-(hydroxymethyl)cyclopropanes in satisfactory yield.

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6

Trudeau, Stéphane, and Pierre Deslongchamps. "Novel synthesis of a highly functionalized cyclopropane derivative." Canadian Journal of Chemistry 81, no. 9 (September 1, 2003): 1003–11. http://dx.doi.org/10.1139/v03-119.

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A model study was carried out to explore the feasibility of synthesizing fused tricyclic ring structures containing a C7C8 double bond juncture (steroid numbering) by employing an SN2' cyclization of a silyl enol ether to displace an allylic acetate as the key step. Instead of the anticipated product, highly functionalized cyclopropanes were obtained. These novel cyclopropane structures are the result of the concomitant 1,2-migration of a dithiane thioether moiety and the eventual displacement of the acetate group, followed by the cyclization of the silyl enol ether.Key words: tricycles, SN2' cyclization, inductive effect, cyclopropane.

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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

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8

Gopinath, Purushothaman, and Srinivasan Chandrasekaran. "Recent Advances in the Chemistry of Doubly Activated Cyclopropanes: Synthesis and Reactivity." Current Organic Chemistry 23, no. 3 (May 9, 2019): 276–312. http://dx.doi.org/10.2174/1385272823666190213114604.

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Diactivated cyclopropanes containing two geminal electron withdrawing groups, commonly called as ‘Doubly Activated Cyclopropanes’ are useful synthons for the synthesis of many interesting natural products and functionalized molecules. These geminal electron withdrawing groups (EWG’s) facilitate the regioselective ring opening of cyclopropanes by polarizing the C-C bond adjacent to it. This polarization also allows them to undergo 1,3 dipolar cycloaddition reactions when substituted with a suitable electron donor substituent at the adjacent carbon (donor-acceptor cyclopropanes) in the presence of suitable dipolarophiles. In this review, we discuss the recent advances in the chemistry of doubly activated cyclopropanes: their synthesis, reactions and applications in total synthesis.

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9

Ledingham, Edward, Christopher Merritt, Christopher Sumby, Michelle Taylor, and Ben Greatrex. "Stereoselective Cyclopropanation of (–)-Levoglucosenone Derivatives Using Sulfonium and Sulfoxonium Ylides." Synthesis 49, no. 12 (March 17, 2017): 2652–62. http://dx.doi.org/10.1055/s-0036-1588971.

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The synthesis of tri- and tetrasubstituted cyclopropanes from 3-aryl-substituted levoglucosenones (LGO) has been developed. In contrast to the unstabilised ylide dimethylsulfonium methylide which gives epoxides from LGO via 1,2-addition, we have found that the soft nucleophile dimethylsulfoxonium methylide affords cyclopropanes in moderate yields from LGO and in excellent yields and stereoselectivity with 3-aryl LGO derivatives. The use of 1,1,3,3-tetramethylguanidine as base in DMSO to generate the ylide provided the best yields and shortest reaction times. Ester stabilised sulfonium ylides could also be used to generate tetrasubstituted cyclopropane derivatives. One of the products was converted into a cyclopropyl lactone via Baeyer–Villiger oxidation to demonstrate the utility of applying cyclopropanation chemistry to LGO.

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10

Song, Xixi, Junbiao Chang, Yuanyuan Zhu, Shuang Zhao, and Minli Zhang. "Diastereoselective Synthesis of Spirobarbiturate-Cyclopropanes through Organobase-Mediated Spirocyclopropanation of Barbiturate-Based Olefins with Benzyl Chlorides." Synthesis 51, no. 04 (November 6, 2018): 899–906. http://dx.doi.org/10.1055/s-0037-1609637.

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The organobase-mediated diastereoselective spirocyclopropanation of barbiturate-based olefins with 2,4-disubstituted benzyl chlorides has been developed. The reactions were carried out efficiently to afford the desired spirobarbiturate-cyclopropanes in up to 95% yield with more than 20:1 dr in favor of anti-isomers. In order to extend synthetic utility of the spiro-products, a Lewis acid induced cyclopropane-ring-expansion isomerization was also demonstrated.

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11

Shi, Yongjia, Qian Gao, and Senmiao Xu. "Iridium-Catalyzed Asymmetric C–H Borylation Enabled by Chiral Bidentate Boryl Ligands." Synlett 30, no. 19 (October 28, 2019): 2107–12. http://dx.doi.org/10.1055/s-0039-1690225.

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Asymmetric synthesis of optically pure organoboron compounds is a topic that has received a number of attentions owing to their particular importance in synthetic chemistry and drug discovery. We herein highlight recent advances in the iridium-catalyzed C–H borylation of diarylmethylamines and cyclopropanes enabled by chiral bidentate boryl ligands.1 Introduction2 Ir-Catalyzed Asymmetric C(sp2)–H Borylation of Diarylmethylamines3 Ir-Catalyzed Enantioselective C(sp3)–H Borylation of Cyclopropanes4 Conclusion

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12

Wu, Wanqing, Zhiming Lin, and Huanfeng Jiang. "Recent advances in the synthesis of cyclopropanes." Organic & Biomolecular Chemistry 16, no. 40 (2018): 7315–29. http://dx.doi.org/10.1039/c8ob01187g.

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Cyclopropanes have gained much attention by virtue of their interesting structure and unique reactivity. This review discusses the recent advances in the synthesis of cyclopropanes, and some of the related applications will be discussed.

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13

Elinson, M. N., E. O. Dorofeeva, A. N. Vereshchagin, and G. I. Nikishin. "Electrochemical synthesis of cyclopropanes." Russian Chemical Reviews 84, no. 5 (May 29, 2015): 485–97. http://dx.doi.org/10.1070/rcr4465.

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14

Armstrong, Robert W., and Karl W. Maurer. "Synthesis of vicinal cyclopropanes." Tetrahedron Letters 36, no. 3 (January 1995): 357–60. http://dx.doi.org/10.1016/0040-4039(94)02269-h.

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15

Hock, Katharina J., Lucas Mertens, and Rene M. Koenigs. "Rhodium catalyzed synthesis of difluoromethyl cyclopropanes." Chemical Communications 52, no. 95 (2016): 13783–86. http://dx.doi.org/10.1039/c6cc07745e.

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16

Adamo, Mauro F. A., and Vivekananda R. Konda. "A multicomponent synthesis of cyclopropanes." Tetrahedron Letters 49, no. 43 (October 2008): 6224–26. http://dx.doi.org/10.1016/j.tetlet.2008.08.033.

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17

Duffault, Jean-Marc, Pascal Hanoteau, Alfredo Parrilla, and Jacques Einhorn. "Synthesis of Regioselectively Deuterated Cyclopropanes." Synthetic Communications 26, no. 17 (September 1996): 3257–65. http://dx.doi.org/10.1080/00397919608004635.

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18

Altamore, Timothy M., Oanh T. K. Nguyen, Quentin I. Churches, Kate Cavanagh, Xuan T. T. Nguyen, Sandhya A. M. Duggan, Guy Y. Krippner, and Peter J. Duggan. "Concise Synthesis of Enantiomerically Pure (1'S,2'R)- and (1'R,2'S)-2S-Amino-3-(2'-aminomethyl-cyclopropyl)propionic Acid: Two E-Diastereoisomers of 4,5-Methano-L-lysine." Australian Journal of Chemistry 66, no. 9 (2013): 1105. http://dx.doi.org/10.1071/ch13309.

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A concise synthesis of both E-isomers of 2S-amino-3-(2′-aminomethyl-cyclopropyl)propionic acid, new methano-l-lysines, is described. The synthetic route includes nine steps from l-methionine, with a key step involving the cyclopropanation of an intermediate E-allylic alcohol. The resultant hydroxymethylcyclopropanes were readily separated and converted into the title α-amino acids. The stereochemistry around the cyclopropane rings was deduced by conducting the cyclopropanation in the presence of N,N,N′,N′-tetramethyl-d-tartaric acid diamide butylboronate, a chiral controller which is known to favour the production of S-hydroxymethyl cyclopropanes from allylic alcohols.

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19

Ramnauth, Jailall, and Edward Lee-Ruff. "Photochemical preparation of cyclopropanes from cyclobutanones." Canadian Journal of Chemistry 79, no. 2 (February 1, 2001): 114–20. http://dx.doi.org/10.1139/v00-175.

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A general method for the preparation of cyclopropanes is reported. Triplet-photosensitized reactions of a series of cyclobutanones give cyclopropanes as the major product. Part 1 describes the synthesis of substituted cyclobutanones used in this study. In Part 2, the photo-reactions of cyclobutanones are reported. Triplet-sensitized reactions of cyclobutanones using acetone as a sensitizer give cyclopropanes as the major non-polar products. The extent of photodecarbonylation seems to be dependent on α-substitution. Electron-donating groups promote decarbonylation while electron-withdrawing groups favour cycloelimination.Key words: photodecarbonylation, cyclobutanones, cyclopropanes, triplet-sensitization.

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20

Ramnauth, Jailall, and Edward Lee-Ruff. "Photodecarbonylation of chiral cyclobutanones." Canadian Journal of Chemistry 75, no. 5 (May 1, 1997): 518–22. http://dx.doi.org/10.1139/v97-060.

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Triplet photosensitized irradiation of 2(S),3(R)-bis[(benzoyloxy)methyl]cyclobutanone gave optically pure (−)E-1(S),2(S)-bis(benzoyloxymethyl)cyclopropane as a major product in the nonpolar fraction along with its stereoisomer and cycloelimination products. The absolute stereochemistry of the chiral cyclopropane was established by independent synthesis and X-ray crystal structure determination of a synthetic precursor. The distribution of decarbonylation and cycloelimination products was inversely dependent on the concentration of the substrate. Irradiation of the same ketone in tetrahydrofuran or benzene gave mostly cycloelimination products. Addition of Michler's ketone increased the ratio of photodecarbonylation, suggesting a triplet state pathway for this process. This was corroborated by the addition of dicyanoethylene, which showed significant quenching of photodecarbonylation. Irradiation of 2(S)-[(benzoyloxy)methyl]cyclobutane in acetone gave the corresponding cyclopropane as the principal product. Keywords: photodecarbonylation, chiral cyclopropanes, cyclobutanones, triplet sensitization.

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21

Herraiz, Ana G., and Marcos G. Suero. "New Alkene Cyclopropanation Reactions Enabled by Photoredox Catalysis via Radical Carbenoids." Synthesis 51, no. 14 (June 11, 2019): 2821–28. http://dx.doi.org/10.1055/s-0037-1611872.

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We describe the recent emergence of a new approach for the synthesis of cyclopropane rings by means of photoredox catalysis. This methodology relies on the photocatalytic generation of radical carbenoids or carbenoid-like radicals as cyclopropanating species, and is characterized by excellent functional group tolerance, chemoselectivity and the ability to form cyclopropanes with excellent control from E/Z alkene mixtures. The mild reaction conditions and employment of user-friendly reagents are highly attractive features that may lead to this approach being used in academic and industrial laboratories.1 Introduction2 Photoredox-Catalyzed Alkene Cyclopropanations with Radical Carbenoids3 Conclusions and Outlook

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22

Schlinquer, Claire, Wei-Sheng Huang, Ling Chen, Thomas Poisson, Xavier Pannecoucke, André B. Charette, and Philippe Jubault. "Rhodium catalysed enantioselective synthesis of mono-(halo)-methyl-cyclopropanes." Organic & Biomolecular Chemistry 17, no. 3 (2019): 472–76. http://dx.doi.org/10.1039/c8ob03041c.

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23

Chang, Meng-Yang, Yi-Chia Chen, and Chieh-Kai Chan. "One-pot synthesis of multifunctionalized cyclopropanes." Tetrahedron 70, no. 13 (April 2014): 2257–63. http://dx.doi.org/10.1016/j.tet.2014.02.024.

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24

Defosseux, Magali, Nicolas Blanchard, Christophe Meyer, and Janine Cossy. "Synthesis of polypropionate subunits from cyclopropanes." Tetrahedron 61, no. 32 (August 2005): 7632–53. http://dx.doi.org/10.1016/j.tet.2005.05.099.

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25

Denton, Justin R., Dinesh Sukumaran, and Huw M. L. Davies. "Enantioselective Synthesis of Trifluoromethyl-Substituted Cyclopropanes." Organic Letters 9, no. 14 (July 2007): 2625–28. http://dx.doi.org/10.1021/ol070714f.

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26

Yoneda, Ryuji, Kazunori Santo, Shinya Harusawa, and Takushi Kurihara. "A New Synthesis of Polysubstituted Cyclopropanes." Synthetic Communications 17, no. 8 (June 1987): 921–27. http://dx.doi.org/10.1080/00397918708063949.

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27

Gaudemar-bardone, F., M. Mladenova, and M. Gaudemar. "Synthesis of Some New Polysubstituted Cyclopropanes." Synthetic Communications 19, no. 1-2 (January 1989): 141–46. http://dx.doi.org/10.1080/00397918908050962.

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28

ELINSON, M. N., S. K. FEDUKOVICH, T. L. LIZUNOVA, and G. I. NIKISHIN. "ChemInform Abstract: Electrochemical Synthesis of Cyclopropanes." ChemInform 27, no. 23 (August 5, 2010): no. http://dx.doi.org/10.1002/chin.199623300.

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29

ARMSTRONG, R. W., and K. W. MAURER. "ChemInform Abstract: Synthesis of Vicinal Cyclopropanes." ChemInform 26, no. 21 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199521291.

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30

Elinson, M. N., E. O. Dorofeeva, A. N. Vereshchagin, and G. I. Nikishin. "ChemInform Abstract: Electrochemical Synthesis of Cyclopropanes." ChemInform 46, no. 41 (September 24, 2015): no. http://dx.doi.org/10.1002/chin.201541245.

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31

Ikeda, Katsuya, Hiroshi Satoh, and Tamotsu Yamamoto. "SYNTHESIS OF CYCLOPROPANES USING S-ETHENYLSULFILIMINES." Organic Preparations and Procedures International 24, no. 5 (October 1992): 548–51. http://dx.doi.org/10.1080/00304949209356727.

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32

Wang, Yongdong, Jing Han, Jie Chen, and Weiguo Cao. "Transition metal-free generation of the acceptor/acceptor-carbene via α-elimination: synthesis of fluoroacetyl cyclopropanes." Chemical Communications 52, no. 41 (2016): 6817–20. http://dx.doi.org/10.1039/c6cc01576j.

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An efficient transition metal-free approach for the generation of acceptor/acceptor-carbene followed by trapping with alkenes to provide fluoroacetyl cyclopropanes has been described. The resulting cyclopropanes could be further converted into the fluoromethyl dihydrofurans or fluorodihydropyrroles through ring-expansion processes.

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33

Niu, Hong-Ying, Cong Du, Ming-Sheng Xie, Yong Wang, Qian Zhang, Gui-Rong Qu, and Hai-Ming Guo. "Diversity-oriented synthesis of acyclic nucleosides via ring-opening of vinyl cyclopropanes with purines." Chemical Communications 51, no. 16 (2015): 3328–31. http://dx.doi.org/10.1039/c4cc09844g.

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34

Wang, Hai-Xia, Wen-Peng Li, Mi-Mi Zhang, Ming-Sheng Xie, Gui-Rong Qu, and Hai-Ming Guo. "Synthesis of chiral pyrimidine-substituted diester D–A cyclopropanes via asymmetric cyclopropanation of phenyliodonium ylides." Chemical Communications 56, no. 78 (2020): 11649–52. http://dx.doi.org/10.1039/d0cc04536e.

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35

Allouche, Emmanuelle M. D., Sylvain Taillemaud, and André B. Charette. "Spectroscopic characterization of (diiodomethyl)zinc iodide: application to the stereoselective synthesis and functionalization of iodocyclopropanes." Chemical Communications 53, no. 69 (2017): 9606–9. http://dx.doi.org/10.1039/c7cc04348a.

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36

Tang, Fan, Peng-Ju Ma, Yun Yao, Yan-Jun Xu, and Chong-Dao Lu. "Divergent synthesis of polysubstituted cyclopropanes and β-silyoxy imidates via switchable additions of N-tert-butanesulfinylimidates to acylsilanes." Chemical Communications 55, no. 26 (2019): 3777–80. http://dx.doi.org/10.1039/c9cc00963a.

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37

Kotozaki, Manato, Soda Chanthamath, Takuji Fujii, Kazutaka Shibatomi, and Seiji Iwasa. "Highly enantioselective synthesis of trifluoromethyl cyclopropanes by using Ru(ii)–Pheox catalysts." Chemical Communications 54, no. 40 (2018): 5110–13. http://dx.doi.org/10.1039/c8cc02286k.

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An asymmetric synthesis of various trifluoromethyl cyclopropanes from olefins, such as vinyl ferrocene, vinyl ethers, vinyl amines, vinyl carbamates and dienes, was achieved by using Ru(ii)–Pheox catalysts.

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38

Wang, Zhe-Hao, Huan-Huan Zhang, Dao-Ming Wang, Peng-Fei Xu, and Yong-Chun Luo. "Lewis acid catalyzed diastereoselective [3+4]-annulation of donor–acceptor cyclopropanes with anthranils: synthesis of tetrahydro-1-benzazepine derivatives." Chemical Communications 53, no. 61 (2017): 8521–24. http://dx.doi.org/10.1039/c7cc04239f.

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39

Anand, Ashish, Jayashree Yenagi, J. Tonannavar, and Manohar V. Kulkarni. "Cyclopropanes in water: a diastereoselective synthesis of substituted 2H-chromen-2-one and quinolin-2(1H)-one linked cyclopropanes." Green Chemistry 18, no. 7 (2016): 2201–5. http://dx.doi.org/10.1039/c5gc02443a.

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A one-pot three component reaction has been developed for the synthesis of substituted cyclopropanes employing 4-bromomethyl-2H-chromen-2-one/quinolin-2(1H)-ones, aromatic aldehydes and activated nitriles.

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40

Brandenberg, Oliver F., Christopher K. Prier, Kai Chen, Anders M. Knight, Zachary Wu, and Frances H. Arnold. "Stereoselective Enzymatic Synthesis of Heteroatom-Substituted Cyclopropanes." ACS Catalysis 8, no. 4 (February 24, 2018): 2629–34. http://dx.doi.org/10.1021/acscatal.7b04423.

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41

Meyers, Albert I., Jeffrey L. Romine, and Steven A. Fleming. "A novel asymmetric synthesis of substituted cyclopropanes." Journal of the American Chemical Society 110, no. 21 (October 1988): 7245–47. http://dx.doi.org/10.1021/ja00229a067.

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42

Nagasawa, Tetsuya, Yasuhiko Handa, Yuka Onoguchi, and Keisuke Suzuki. "Stereoselective Synthesis of Cyclopropanes via Homoallylic Participation." Bulletin of the Chemical Society of Japan 69, no. 1 (January 1996): 31–39. http://dx.doi.org/10.1246/bcsj.69.31.

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43

Ruano, Jose´ L. Garci´a, Ana M. Marti´n Castro, and Esther Torrente. "Efficient Enantioselective Synthesis of Cyclopropanes from Sulfonylpyrazolines." Phosphorus, Sulfur, and Silicon and the Related Elements 180, no. 5-6 (March 2, 2005): 1445–46. http://dx.doi.org/10.1080/10426500590913014.

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44

Wang, Yi, Xiaoming Zhao, Youhua Li, and Long Lu. "Stereospecific synthesis of trifluoromethyl-substituted polyfunctionalized cyclopropanes." Tetrahedron Letters 45, no. 41 (October 2004): 7775–77. http://dx.doi.org/10.1016/j.tetlet.2004.08.064.

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45

Daniel, Méndez I., Klimova Tatiana, Klimova Elena, Hernández O. Simon, Perez F. Javier, and G. Marcos Martı́nez. "Synthesis of di- and monobromo(ferrocenylvinyl)cyclopropanes." Journal of Organometallic Chemistry 689, no. 15 (August 2004): 2503–10. http://dx.doi.org/10.1016/j.jorganchem.2004.04.044.

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46

Risatti, Christina A., and Richard E. Taylor. "Enantioselective Synthesis of Cyclopropanes by Aldehyde Homologation." Angewandte Chemie International Edition 43, no. 48 (December 10, 2004): 6671–72. http://dx.doi.org/10.1002/anie.200461106.

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ELINSON, M. N., S. K. FEDUKOVICH, T. L. LIZUNOVA, and G. I. NIKISHIN. "ChemInform Abstract: The Electrochemical Synthesis of Cyclopropanes." ChemInform 27, no. 31 (August 5, 2010): no. http://dx.doi.org/10.1002/chin.199631248.

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Risatti, Christina A., and Richard E. Taylor. "Enantioselective Synthesis of Cyclopropanes by Aldehyde Homologation." Angewandte Chemie 116, no. 48 (December 10, 2004): 6839–40. http://dx.doi.org/10.1002/ange.200461106.

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DUFFAULT, J. M., P. HANOTEAU, A. PARRILLA, and J. EINHORN. "ChemInform Abstract: Synthesis of Regioselectively Deuterated Cyclopropanes." ChemInform 27, no. 48 (August 4, 2010): no. http://dx.doi.org/10.1002/chin.199648091.

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Cossy, Janine. "Stereoselective Synthesis of Cyclopropanes Bearing Adjacent Stereocenters." Synthesis 1999, no. 06 (June 1999): 1063–75. http://dx.doi.org/10.1055/s-1999-3507.

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