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Journal articles on the topic 'Cyclopropanol chiral'

Author: Grafiati

Published: 4 June 2021

Last updated: 7 February 2022

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1

Kim, Taejin, Amude M. Kassim, Ajit Botejue, Chen Zhang, Jared Forte, David Rozzell, Mark A. Huffman, Paul N. Devine, and John A. McIntosh. "Hemoprotein‐Catalyzed Cyclopropanation En Route to the Chiral Cyclopropanol Fragment of Grazoprevir." ChemBioChem 20, no. 9 (March 6, 2019): 1129–32. http://dx.doi.org/10.1002/cbic.201800652.

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2

Csuk, René, and Anja Kern. "Synthesis of Rigid Cyclopropanoid Nucleoside Analogues." Zeitschrift für Naturforschung B 57, no. 10 (October 1, 2002): 1169–73. http://dx.doi.org/10.1515/znb-2002-1015.

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A convenient synthesis has been developed for the synthesis of cyclopropanoid nucleoside analogues that possess no additional spacer groups between the heterocycle and the hydroxylated cyclopropane ring. For some of these compounds the respective enantiomers could be separated on an analytical scale by means of HPLC using chiral phases.

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3

Csuk, René, and Gisela Thiede. "Synthesis of Spacered Nucleoside Analogues Comprising a Difluorocyclopropane Moiety." Zeitschrift für Naturforschung B 58, no. 9 (September 1, 2003): 853–60. http://dx.doi.org/10.1515/znb-2003-0907.

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A novel class of difluorinated cyclopropanoic nucleoside analogues containing a propyl spacer between the cyclopropane ring and the heterocycle has been prepared. Some of these compounds showed weak antitumor activity in prelimary screenings. The resolution of these racemic compounds on an analytical scale was performed by HPLC using chiral stationary phases.

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4

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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5

Bassan, Ephraim M., Carl A. Baxter, Gregory L. Beutner, Khateeta M. Emerson, Fred J. Fleitz, Simon Johnson, Stephen Keen, et al. "Multikilogram-Scale Synthesis of a Chiral Cyclopropanol and an Investigation of the Safe Use of Lithium Acetylide–Ethylene Diamine Complex." Organic Process Research & Development 16, no. 1 (December 7, 2011): 87–95. http://dx.doi.org/10.1021/op2002497.

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6

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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7

Barysevich, Maryia V., Volha V. Kazlova, Aliaksandr G. Kukel, Aliaksandra I. Liubina, Alaksiej L. Hurski, Vladimir N. Zhabinskii, and Vladimir A. Khripach. "Stereoselective synthesis of α-methyl and α-alkyl ketones from esters and alkenesviacyclopropanol intermediates." Chemical Communications 54, no. 22 (2018): 2800–2803. http://dx.doi.org/10.1039/c8cc00888d.

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8

Shen, Yue, Peng-Fei Yang, Gaosheng Yang, Wen-Long Chen, and Zhuo Chai. "Lewis acid-catalyzed enantiospecific [3 + 2] annulations of γ-butyrolactone fused cyclopropanes with aromatic aldehydes: synthesis of chiral furanolignans." Organic & Biomolecular Chemistry 16, no. 15 (2018): 2688–96. http://dx.doi.org/10.1039/c8ob00455b.

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9

Xie, Ming-Sheng, Yong Wang, Jian-Ping Li, Cong Du, Yan-Yan Zhang, Er-Jun Hao, Yi-Ming Zhang, Gui-Rong Qu, and Hai-Ming Guo. "A straightforward entry to chiral carbocyclic nucleoside analogues via the enantioselective [3+2] cycloaddition of α-nucleobase substituted acrylates." Chemical Communications 51, no. 62 (2015): 12451–54. http://dx.doi.org/10.1039/c5cc04832j.

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10

Delion, Laëtitia, Thomas Poisson, Philippe Jubault, Xavier Pannecoucke, and André B. Charette. "Synthesis of fluorocyclopropanes via the enantioselective cyclopropanation of fluoro-substituted allylic alcohols using zinc carbenoids." Canadian Journal of Chemistry 98, no. 9 (September 2020): 516–23. http://dx.doi.org/10.1139/cjc-2020-0036.

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Cyclopropanation reactions using zinc carbenoids are a powerful means to access cyclopropanes. Described herein is an enantioselective version of the reaction using zinc reagents and a chiral dioxaborolane ligand in the generation of fluorocyclopropanes. Readily available 2- and 3-fluoroallylic alcohols were efficiently cyclopropanated in high yields and excellent enantioselectivities. This method provides access to a variety of structurally diverse chiral fluorocyclopropanes that can be used as useful chiral building blocks.

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11

Nie, Guihua, Xuan Huang, Zhongyao Wang, Dingwu Pan, Junmin Zhang, and Yonggui Robin Chi. "Umpolung of donor–acceptor cyclopropanes via N-heterocyclic carbene organic catalysis." Organic Chemistry Frontiers 8, no. 18 (2021): 5105–11. http://dx.doi.org/10.1039/d1qo00826a.

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A carbene-catalyzed formal umpolung of donor–acceptor (D–A) cyclopropanes is disclosed with chiral spirocyclic lactones bearing multiple functional groups afforded with excellent enantio- and diastereoselectivities.

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12

Baldwin, John E., and Stephanie R. Singer. "Efficient syntheses of four chiral phenylcyclopropanes." Canadian Journal of Chemistry 86, no. 5 (May 1, 2008): 395–400. http://dx.doi.org/10.1139/v08-033.

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An efficient four-step synthetic route from each of four crystalline isotopically labeled (1R)-menthyl (1S,2S)-(+)-2-phenylcyclopropanecarboxyates of better than 99% enantiomeric excess has provided multi-gram quantities of the corresponding chiral phenylcyclopropanes. The key transformation involved a bis[1,3-bis(diphenylphosphino)propane]rhodium chloride that catalyzed a highly stereoselective decarbonylation of a trans-2-phenylcyclopropanecarboxaldehyde.Key words: cyclopropanes chiral thanks to isotopic substituents, catalytic decarbonylations of cyclopropanecarboxaldehydes.

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13

Kelly, Richard. "Expression of concern: Enantio- and diastereocontrolled conversion of chiral epoxides to trans-cyclopropane carboxylates: application to the synthesis of cascarillic acid, grenadamide and l-(−)-CCG-II." Organic & Biomolecular Chemistry 15, no. 27 (2017): 5853. http://dx.doi.org/10.1039/c7ob90107k.

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Expression of concern for ‘Enantio- and diastereocontrolled conversion of chiral epoxides to trans-cyclopropane carboxylates: application to the synthesis of cascarillic acid, grenadamide and l-(−)-CCG-II’ by Pradeep Kumar et al., Org. Biomol. Chem., 2012, 10, 6987–6994.

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14

Csuk, René, and Gisela Thiede. "Synthese difluorierter cyclopropanoider Nucleosidanaloga/Synthesis of Difluorinated Cyclopropanoid Nucleoside Analogues." Zeitschrift für Naturforschung B 57, no. 11 (November 1, 2002): 1287–94. http://dx.doi.org/10.1515/znb-2002-1115.

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Starting from (2,2-difluorocyclopropyl)methanol a novel class of difluorinated cyclopropanoid nucleoside analogues containing two hydroxymethyl side chains was synthesized in a straightforward way. Several of the final compounds could be obtained in an enantiomerically pure form by HPLC using chiral stationary phases.

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15

Freedman, Teresa B., Diane L. Hausch, Steven J. Cianciosi, and John E. Baldwin. "Kinetics of thermal racemization of (2S,3S)-1-13C-1,2,3-d3-cyclopropane followed by vibrational circular dichroism spectroscopy." Canadian Journal of Chemistry 76, no. 6 (June 1, 1998): 806–10. http://dx.doi.org/10.1139/v98-070.

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Vibrational circular dichoism spectra recorded for (2S,3S)-1-13C-1,2,3-d3-cyclopropane and for mixtures of it and the three related stereoisomers prepared through gas-phase thermal stereomutation reactions at 407°C lead to the rate constant for racemization: kα = (4k1 + 4k12) = (3.12 ± 0.04) x 10-5 s-1. This and the rate constant measured for geometrical equilibration between the two chiral and the two achiral stereoisomers of 1-13C-1,2,3-d3-cyclopropane, ki = (8k1 + 4k12) = (4.63 ± 0.20) x 10-5 s-1, give two equations in two unknowns, and allow one to solve for one-center (k1) and two-center (k12) epimerization rate constants for cyclopropane stereomutations. They are nearly equal, a clear indication of closely competitive reaction pathways.Key words: cyclopropane stereomutations, thermal epimerizations, chirality through deuterium and carbon-13 labeling, vibrational circular dichroism.

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16

Csuk, René, and Anja Kern. "Synthesis of Cyclopropanoid Nucleoside Analogues Possessing a Flexible Side Chain." Zeitschrift für Naturforschung B 58, no. 9 (September 1, 2003): 843–52. http://dx.doi.org/10.1515/znb-2003-0906.

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A novel class of cyclopropanoic nucleoside analogues containing an hydroxyethyl residue instead of a hydroxymethyl side chain has been prepared in an easy sequence. These compounds showed weak antitumor activity. The resolution of the racemates on an analytical scale was performed by HPLC using chiral stationary phases.

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17

Valeev, F. A., E. V. Gorobets, and M. S. Miftakhov. "3-Iodolevoglucosenone and chiral cyclopropane." Russian Chemical Bulletin 46, no. 6 (June 1997): 1192–93. http://dx.doi.org/10.1007/bf02496232.

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18

Kumar, Pradeep, Abhishek Dubey, and Anand Harbindu. "Correction and removal of expression of concern: Enantio- and diastereocontrolled conversion of chiral epoxides to trans-cyclopropane carboxylates: application to the synthesis of cascarillic acid, grenadamide and l-(−)-CCG-II." Organic & Biomolecular Chemistry 18, no. 27 (2020): 5264. http://dx.doi.org/10.1039/d0ob90090g.

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Correction and removal of expression of concern for ‘Enantio- and diastereocontrolled conversion of chiral epoxides to trans-cyclopropane carboxylates: application to the synthesis of cascarillic acid, grenadamide and l-(−)-CCG-II’ by Pradeep Kumar et al., Org. Biomol. Chem., 2012, 10, 6987–6994, DOI: 10.1039/C2OB25622C.

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19

Ružena, Čižmáriková, Habala Ladislav, and Markuliak Mário. "Celkové inhalačné anestetiká – farmakodynamika, farmakokinetika a chirálne vlastnosti." Česká a slovenská farmacie 70, no. 1 (2021): 7–17. http://dx.doi.org/10.5817/csf2021-1-7.

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Since the advent of nitric oxide, diethyl ether, chloroform and cyclopropane, the greatest advancement in the area of general inhalational anesthetics has been achieved by the introduction of fluorinated anesthetics and the relevant chiral techniques. This progress led to marked decrease in mortality rates in anesthesia. In the group of chiral fluorinated compounds, halothane (Fluotan®), isoflurane (Foran®), desflurane (Supran®) and enflurane (Ehran®) are deployed as volatile anesthetics. Chiral anesthetics possess a stereogenic center in their molecules and thus exist as two enantiomers (S)-(+) and (R)-(–). Although these chiral anesthetics are used as racemates, it is crucial to study besides the bioactivities of the racemic compounds also the biological activity and other properties of the particular enantiomers. The present survey discusses the drug category known as inhalational anesthetics in regard to their chiral aspects. These compounds exhibit marked differences between the (R) and (S)-enantiomers in their pharmacodynamics, pharmacokinetics and toxicity. The main analytical technique employed in the enantioseparation of these compounds is gas chromatography (GC). This review lists the individual chiral phases (chiral selectors) used in the enantioseparation as well as in pharmacokinetic studies. The possibilities of preparation of these compounds in their enantiomerically pure form by means of stereoselective synthesis are also mentioned.

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20

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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21

Taylor, Dennis K. "ChemInform Abstract: Novel Approaches to Chiral Cyclopropanes." ChemInform 33, no. 51 (May 18, 2010): no. http://dx.doi.org/10.1002/chin.200251262.

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22

VALEEV, F. A., E. V. GOROBETS, and M. S. MIFTAKHOV. "ChemInform Abstract: 3-Iodolevoglucosenone and Chiral Cyclopropane." ChemInform 28, no. 48 (August 2, 2010): no. http://dx.doi.org/10.1002/chin.199748253.

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23

Satska, Yulia A., Elena A. Mikhalyova, Zhanna V. Chernenko, Sergey V. Kolotilov, Matthias Zeller, Igor V. Komarov, Andriy V. Tymtsunik, Andrey Tolmachev, Konstantin S. Gavrilenko, and Anthony W. Addison. "Sorption discrimination between secondary alcohol enantiomers by chiral alkyl-dicarboxylate MOFs." RSC Advances 6, no. 96 (2016): 93707–14. http://dx.doi.org/10.1039/c6ra09353a.

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The coordination polymers withtrans-(S,S)-1,2-cyclopropane dicarboxylate or (1R,3S)-camphorate contain only one polar group in close proximity to the asymmetric C atom but show different sorption of (R) or (S) isomers of 2-butanol.

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24

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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25

Rubina, Marina, William M. Sherrill, Alexey Yu Barkov, and Michael Rubin. "Rational design of cyclopropane-based chiral PHOX ligands for intermolecular asymmetric Heck reaction." Beilstein Journal of Organic Chemistry 10 (July 7, 2014): 1536–48. http://dx.doi.org/10.3762/bjoc.10.158.

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A novel class of chiral phosphanyl-oxazoline (PHOX) ligands with a conformationally rigid cyclopropyl backbone was synthesized and tested in the intermolecular asymmetric Heck reaction. Mechanistic modelling and crystallographic studies were used to predict the optimal ligand structure and helped to design a very efficient and highly selective catalytic system. Employment of the optimized ligands in the asymmetric arylation of cyclic olefins allowed for achieving high enantioselectivities and significantly suppressing product isomerization. Factors affecting the selectivity and the rate of the isomerization were identified. It was shown that the nature of this isomerization is different from that demonstrated previously using chiral diphosphine ligands.

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26

Zhang, Yan, Jiang Pan, Zheng-Jiao Luan, Guo-Chao Xu, Sunghoon Park, and Jian-He Xu. "Cloning and Characterization of a Novel Esterase from Rhodococcus sp. for Highly Enantioselective Synthesis of a Chiral Cilastatin Precursor." Applied and Environmental Microbiology 80, no. 23 (September 19, 2014): 7348–55. http://dx.doi.org/10.1128/aem.01597-14.

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ABSTRACTA novel nonheme chloroperoxidase (RhEst1), with promiscuous esterase activity for enantioselective hydrolysis of ethyl (S)-2,2-dimethylcyclopropanecarboxylate, was identified from a shotgun library ofRhodococcussp. strain ECU1013.RhEst1 was overexpressed inEscherichia coliBL21(DE3), purified to homogeneity, and functionally characterized. Fingerprinting analysis revealed thatRhEst1 preferspara-nitrophenyl (pNP) esters of short-chain acyl groups.pNP esters with a cyclic acyl moiety, especially that with a cyclobutanyl group, were also substrates forRhEst1. TheKmvalues for methyl 2,2-dimethylcyclopropanecarboxylate (DmCpCm) and ethyl 2,2-dimethylcyclopropane carboxylate (DmCpCe) were 0.25 and 0.43 mM, respectively.RhEst1 could serve as an efficient hydrolase for the bioproduction of optically pure (S)-2,2-dimethyl cyclopropane carboxylic acid (DmCpCa), which is an important chiral building block for cilastatin. As much as 0.5 M DmCpCe was enantioselectively hydrolyzed into (S)-DmCpCa, with a molar yield of 47.8% and an enantiomeric excess (ee) of 97.5%, indicating an extremely high enantioselectivity (E= 240) of this novel and unique biocatalyst for green manufacturing of highly valuable chiral chemicals.

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27

Yu, Jurong, Jing-Yu Lai, Jianhua Ye, Narayanan Balu, L. Manmohan Reddy, Wenhu Duan, Elaine R. Fogel, Jorge H. Capdevila, and J. R. Falck. "Chiral cyclopropanes: asymmetric synthesis of constanolactones A and B." Tetrahedron Letters 43, no. 21 (May 2002): 3939–41. http://dx.doi.org/10.1016/s0040-4039(02)00699-8.

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28

Simonneaux, Gérard, Paul Le Maux, and Sandrine Juillard. "Asymmetric Synthesis of Trifluoromethylphenyl Cyclopropanes Catalyzed by Chiral Metalloporphyrins." Synthesis 2006, no. 10 (May 2006): 1701–4. http://dx.doi.org/10.1055/s-2006-926451.

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29

Inuki, Shinsuke, Ippei Ohta, Shunichi Ishibashi, Masayuki Takamatsu, Koichi Fukase, and Yukari Fujimoto. "Total Synthesis of Cardiolipins Containing Chiral Cyclopropane Fatty Acids." Journal of Organic Chemistry 82, no. 15 (July 19, 2017): 7832–38. http://dx.doi.org/10.1021/acs.joc.7b00945.

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30

Ghanem, Ashraf, Hassan Y. Aboul-Enein, and Paul Müller. "One-pot synthesis and chiral analysis of cyclopropane derivatives." Chirality 17, no. 1 (November 3, 2004): 44–50. http://dx.doi.org/10.1002/chir.20093.

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31

Huang, Hui, and Qinghua Chen. "Synthesis of spiro-cyclopropane derivatives containing multiple chiral centers." Science in China Series B: Chemistry 42, no. 3 (June 1999): 268–76. http://dx.doi.org/10.1007/bf02874242.

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32

Taniguchi, Takashi, Yasuaki Taketomo, Mizuki Moriyama, Noritada Matsuo, and Yoo Tanabe. "Synthesis and Stereostructure-Activity Relationship of Novel Pyrethroids Possessing two Asymmetric Centers on a Cyclopropane Ring." Molecules 24, no. 6 (March 14, 2019): 1023. http://dx.doi.org/10.3390/molecules24061023.

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2-Methylcyclopropane pyrethroid insecticides bearing chiral cyanohydrin esters or chiral ethers and two asymmetric centers on the cyclopropane ring, were synthesized. These compounds were designed using a “reverse connection approach” between the isopropyl group in Fenvalerate, and between two dimethyl groups in an Etofenprox analogue (the methyl, ethyl form), respectively. These syntheses were achieved by accessible ring opening reactions of commercially available (±)-, (R)-, and (S)-propylene oxides using 4-chlorobenzyl cyanide anion as the crucial step, giving good overall yield of the product with >98% ee. The insecticidal activity against the common mosquito (Culex pipiens pallens) was assessed for pairs of achiral diastereomeric (1R*,2S*)-, (1R*,2R*)-cyanohydrin esters, and (1R*,2S*)-, (1R*,2R*)-ethers; only the (1R*,2R*)-ether was significantly effective. For the enantiomeric (1S,2S)-ether and (1R,2R)-ether, the activity was clearly centered on the (1R,2R)-ether. The present stereostructure‒activity relationship revealed that (i) cyanohydrin esters derived from fenvalerate were unexpectedly inactive, whereas ethers derived from etofenprox were active, and (ii) apparent chiral discrimination between the (1S,2S)-ether and the (1R,2R)-ether was observed. During the present synthetic study, we performed alternative convergent syntheses of Etofenprox and novel 4-EtO-type (1S,2S)- and (1R,2R)-pyrethroids from the corresponding parent 4-Cl-type pyrethroids, by utilizing a recently-developed hydroxylation cross-coupling reaction.

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33

Samet, Alexander V., Anatolly M. Shestopalov, Dmitriy N. Lutov, Lyudmila A. Rodinovskaya, Alexander A. Shestopalov, and Victor V. Semenov. "Preparation of chiral cyclopropanes with a carbohydrate fragment from levoglucosenone." Tetrahedron: Asymmetry 18, no. 16 (August 2007): 1986–89. http://dx.doi.org/10.1016/j.tetasy.2007.08.013.

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34

Muray, Elena, Ona Illa, José A. Castillo, Ángel Álvarez-Larena, José L. Bourdelande, Vicenç Branchadell, and Rosa M. Ortuño. "Photolysis of Chiral 1-Pyrazolines to Cyclopropanes: Mechanism and Stereospecificity." Journal of Organic Chemistry 68, no. 12 (June 2003): 4906–11. http://dx.doi.org/10.1021/jo0342471.

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35

Wang, Xiaoxu, Jing Ke, Yiling Zhu, Arghya Deb, Yijie Xu, and X. Peter Zhang. "Asymmetric Radical Process for General Synthesis of Chiral Heteroaryl Cyclopropanes." Journal of the American Chemical Society 143, no. 29 (July 20, 2021): 11121–29. http://dx.doi.org/10.1021/jacs.1c04655.

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36

Kumar, Pradeep, Abhishek Dubey, and Anand Harbindu. "Enantio- and diastereocontrolled conversion of chiral epoxides to trans-cyclopropane carboxylates: application to the synthesis of cascarillic acid, grenadamide and l-(−)-CCG-II." Organic & Biomolecular Chemistry 10, no. 34 (2012): 6987–94. http://dx.doi.org/10.1039/c2ob25622c.

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A very concise and practical synthesis of cascarillic acid, grenadamide and l-CCG-II, a cyclopropane containing natural products is accomplished employing Wadsworth-Emmons cyclopropanation reaction as key step.

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37

Pedroni, Julia, and Nicolai Cramer. "Chiral γ-Lactams by Enantioselective Palladium(0)-Catalyzed Cyclopropane Functionalizations." Angewandte Chemie 127, no. 40 (August 12, 2015): 11992–95. http://dx.doi.org/10.1002/ange.201505916.

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38

Pedroni, Julia, and Nicolai Cramer. "Chiral γ-Lactams by Enantioselective Palladium(0)-Catalyzed Cyclopropane Functionalizations." Angewandte Chemie International Edition 54, no. 40 (August 12, 2015): 11826–29. http://dx.doi.org/10.1002/anie.201505916.

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39

Hanna, George M., and Cesar A. Lau-Cam. "Determination of Enantiomeric Purity of Tranylcypromine Sulfate by Proton Magnetic Resonance Spectroscopy with Chiral Lanthanide Shift Reagent." Journal of AOAC INTERNATIONAL 72, no. 4 (July 1, 1989): 552–55. http://dx.doi.org/10.1093/jaoac/72.4.552.

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Abstract Optimum experimental conditions were developed for determination of the optical purity of samples of tranylcypromine sulfate by proton magnetic resonance spectroscopy after complexation with the chiral lanthanide chelate Eu(hfc).3. At a substrate concentration of 0.25M (0.125M as sulfate) in CDC13 and an Eu(hfc)3 to substrate molar ratio of 1, the methine proton geminal to the amino group in the cyclopropane ring showed the largest induced shift and largest enantiomeric induced shift difference. From the relative intensities of the resolved (+)-CH-NH2 protons (15.77 ppm) and (-)-CH-NH2 proton (16.04 ppm), the enantiomeric purity and percentage compositions were readily calculated. The mean ± SD recovery of (+)- tranylcypromine sulfate from synthetic enantiomeric mixtures was 101.02 ± 2.59 (n = 6).

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Baldwin, John E., and Steven J. Cianciosi. "Syntheses of racemic and both chiral forms of cyclopropane-1,2-d2 and cyclopropane-1-13C-1,2,3-d3." Journal of the American Chemical Society 114, no. 24 (November 1992): 9401–8. http://dx.doi.org/10.1021/ja00050a020.

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Norsikian, Stephanie, Ilane Marek, Jean-François Poisson, and Jean F. Normant. "Enantioselective Carbolithiation of Cinnamyl Acetals. New Access to Chiral Disubstituted Cyclopropanes." Journal of Organic Chemistry 62, no. 15 (July 1997): 4898–99. http://dx.doi.org/10.1021/jo9705172.

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Dieckmann, Michael, Yun-Suk Jang, and Nicolai Cramer. "Chiral Cyclopentadienyl Iridium(III) Complexes Promote Enantioselective Cycloisomerizations Giving Fused Cyclopropanes." Angewandte Chemie 127, no. 41 (August 27, 2015): 12317–20. http://dx.doi.org/10.1002/ange.201506483.

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Dieckmann, Michael, Yun-Suk Jang, and Nicolai Cramer. "Chiral Cyclopentadienyl Iridium(III) Complexes Promote Enantioselective Cycloisomerizations Giving Fused Cyclopropanes." Angewandte Chemie International Edition 54, no. 41 (August 27, 2015): 12149–52. http://dx.doi.org/10.1002/anie.201506483.

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MICHELET, V., and J. P. GENET. "ChemInform Abstract: A Palladium-Catalyzed Route to Chiral 1,2,3-Trisubstituted Cyclopropanes." ChemInform 28, no. 10 (August 4, 2010): no. http://dx.doi.org/10.1002/chin.199710075.

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Yu, Jurong, Jing-Yu Lai, Jianhua Ye, Narayanan Balu, L. Manmohan Reddy, Wenhu Duan, Elaine R. Fogel, Jorge H. Capdevila, and J. R. Falck. "ChemInform Abstract: Chiral Cyclopropanes: Asymmetric Synthesis of Constanolactones A and B." ChemInform 33, no. 36 (May 20, 2010): no. http://dx.doi.org/10.1002/chin.200236218.

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Cheeseman, Matt, Fred J. P. Feuillet, Andrew L. Johnson, and Steven D. Bull. "A novel strategy for the asymmetric synthesis of chiral cyclopropane carboxaldehydes." Chemical Communications, no. 18 (2005): 2372. http://dx.doi.org/10.1039/b501847a.

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BALDWIN, J. E., and S. J. CIANCIOSI. "ChemInform Abstract: Syntheses of Racemic and Both Chiral Forms of Cyclopropane-1,2-d2 and Cyclopropane-1-13C-1,2,3-d3." ChemInform 24, no. 14 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199314125.

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Nishii, Yoshinori. "Highly Stereoselective Construction and Chiral Transfer Ring-expansion of Highly Substituted Cyclopropanes." Journal of Synthetic Organic Chemistry, Japan 73, no. 7 (2015): 701–12. http://dx.doi.org/10.5059/yukigoseikyokaishi.73.701.

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Companyó, Xavier, Andrea-Nekane Alba, Francisco Cárdenas, Albert Moyano, and Ramon Rios. "Asymmetric Organocatalytic Cyclopropanation - Highly Stereocontrolled Synthesis of Chiral Cyclopropanes with Quaternary Stereocenters." European Journal of Organic Chemistry 2009, no. 18 (June 2009): 3075–80. http://dx.doi.org/10.1002/ejoc.200900209.

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Companyó, Xavier, Andrea-Nekane Alba, Francisco Cárdenas, Albert Moyano, and Ramon Rios. "Asymmetric Organocatalytic Cyclopropanation - Highly Stereocontrolled Synthesis of Chiral Cyclopropanes with Quaternary Stereocenters." European Journal of Organic Chemistry 2009, no. 24 (August 2009): 4180. http://dx.doi.org/10.1002/ejoc.200900690.

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