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Journal articles on the topic 'Homochiral synthesis'

Author: Grafiati

Published: 4 June 2021

Last updated: 15 February 2022

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1

Baker, Stephen J., Kenneth J. M. Beresford, and Douglas W. Young. "Synthesis of homochiral tetrahydropteridines." Tetrahedron 70, no. 40 (October 2014): 7221–28. http://dx.doi.org/10.1016/j.tet.2014.06.048.

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2

Kjeldsen, Niels Due, Erik Daa Funder, and Kurt V. Gothelf. "Synthesis of homochiral tris-indanyl molecular rods." Org. Biomol. Chem. 12, no. 22 (2014): 3679–85. http://dx.doi.org/10.1039/c4ob00011k.

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3

Lohray, Braj B., and Jaimala R. Ahuja. "Synthesis of homochiral amino alcohols, aziridines and diamines via homochiral cyclic sulphites." Journal of the Chemical Society, Chemical Communications, no. 2 (1991): 95. http://dx.doi.org/10.1039/c39910000095.

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4

Hill, Bryan, Robert Jordan, Yang Qu, Abdeljalil Assoud, and Russell Rodrigo. "A common synthetic route to homochiral tetracycles related to pillaromycinone and premithramycinone." Canadian Journal of Chemistry 89, no. 12 (December 2011): 1457–68. http://dx.doi.org/10.1139/v11-119.

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Homochiral AB segments for (+)- and (–)-pillaromycinone were prepared in 11 steps from 2-acetylfuran. The synthesis featured an intramolecular Diels–Alder reaction of a 2,5-disubstituted furan and a hydroxyl-directed homogeneous hydrogenation of the tetrasubstituted alkene double bond of two enones. The CD segment was attached by a modified Staunton–Weinreb annulation to produce the desired homochiral tetracycle 21c related to (+)-pillaromycinone. An unusual acetonide migration enabled the synthesis of a tetracyclic model for premithramycinone.

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5

YAMAMOTO, Hisashi, and Atsunori MORI. "Chiralsynthon? Homochiral acetal in organic synthesis." Journal of Synthetic Organic Chemistry, Japan 45, no. 10 (1987): 944–56. http://dx.doi.org/10.5059/yukigoseikyokaishi.45.944.

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6

Alker, David, D. Neville Jones, G. Mark Taylor, and William W. Wood. "Synthesis of homochiral trisubstituted γ-butyrolactones." Tetrahedron Letters 32, no. 13 (March 1991): 1667–70. http://dx.doi.org/10.1016/s0040-4039(00)74300-0.

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7

Abad, Antonio, Consuelo Agulló, Manuel Arnó, Ana C. Cuñat, Benjamín Meseguer, and Ramón J. Zaragozá. "Synthesis of Homochiral Phenanthrones from Carvone." Synlett 1994, no. 09 (1994): 733–35. http://dx.doi.org/10.1055/s-1994-22990.

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8

Baker, Stephen J., Kenneth J. M. Beresford, and Douglas W. Young. "ChemInform Abstract: Synthesis of Homochiral Tetrahydropteridines." ChemInform 46, no. 9 (February 16, 2015): no. http://dx.doi.org/10.1002/chin.201509238.

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9

Lu, Peng, Luis Gómez-Hortigüela, Lei Xu, and Miguel A. Camblor. "Synthesis of STW zeolites using imidazolium-based dications of varying length." Journal of Materials Chemistry A 6, no. 4 (2018): 1485–95. http://dx.doi.org/10.1039/c7ta10002g.

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10

Skolnick, Jeffrey, and Mu Gao. "On the emergence of homochirality and life itself." Biochemist 43, no. 1 (January 20, 2021): 4–12. http://dx.doi.org/10.1042/bio20210002.

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Many of life’s molecules including proteins are built from chiral building blocks. What drove homochiral building block selection? Simulations on demi-chiral proteins containing equal numbers of d- and l-amino acids show that they possess many modern homochiral protein properties. They have the same global folds and could do the same biochemistry, with ancient, essential functions being most prevalent. They could synthesize chiral RNA and lipids which formed vesicles. RNA eventually combined with proteins creating ribosomes for more efficient protein synthesis, and thus, life began. Increased native state stability from homochiral secondary structure hydrogen bonding helped drive proteins towards homochirality.

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11

Lohray, B. Bhushan, Yun Gao, and K. Barry Sharpless. "One pot synthesis of homochiral aziridines and aminoalcohols from homochiral 1,2-cyclic sulfates." Tetrahedron Letters 30, no. 20 (January 1989): 2623–26. http://dx.doi.org/10.1016/s0040-4039(00)99081-6.

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12

Zhang, Guangju, Siqi Xiu, Ying Wei, Qingguo Zhang, and Kedi Cai. "Design and synthesis of nanoporous carbon materials using Cd-based homochiral metal–organic frameworks as precursors for supercapacitor application." CrystEngComm 20, no. 31 (2018): 4364–69. http://dx.doi.org/10.1039/c8ce01027g.

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13

Chang, Cui-Lan, Xiao-Yue Qi, Jiang-Wei Zhang, Ya-Ming Qiu, Xian-Jiang Li, Xin Wang, Yu Bai, Jun-Liang Sun, and Hu-Wei Liu. "Facile synthesis of magnetic homochiral metal–organic frameworks for “enantioselective fishing”." Chemical Communications 51, no. 17 (2015): 3566–69. http://dx.doi.org/10.1039/c4cc09988e.

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14

Mash, Eugene A., and Keith A. Nelson. "Homochiral ketals in organic synthesis. Diastereoselective cyclopropanation." Journal of the American Chemical Society 107, no. 26 (December 1985): 8256–58. http://dx.doi.org/10.1021/ja00312a073.

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15

Liotta, Louis J., and Bruce Ganem. "A Short Homochiral Synthesis of Substituted Pyrrolidines." Synlett 1990, no. 09 (1990): 503–4. http://dx.doi.org/10.1055/s-1990-21142.

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16

Cox, Paul J., and Nigel S. Simpkins. "Asymmetric synthesis using homochiral lithium amide bases." Tetrahedron: Asymmetry 2, no. 1 (January 1991): 1–26. http://dx.doi.org/10.1016/s0957-4166(00)82150-3.

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17

Ng, Karno, Ratnasamy Somanathan, and Patrick J. Walsh. "Synthesis of homochiral pentadentate sulfonamide-based ligands." Tetrahedron: Asymmetry 12, no. 12 (July 2001): 1719–22. http://dx.doi.org/10.1016/s0957-4166(01)00292-0.

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18

Davies, Stephen G., Andrew W. Mulvaney, Angela J. Russell, and Andrew D. Smith. "Parallel synthesis of homochiral β-amino acids." Tetrahedron: Asymmetry 18, no. 13 (July 2007): 1554–66. http://dx.doi.org/10.1016/j.tetasy.2007.06.008.

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19

Alker, David, D. Neville Jones, G. Mark Taylor, and William W. Wood. "General synthesis of homochiral trisubstituted γ-butyrolactones." J. Chem. Soc., Perkin Trans. 1, no. 9 (1992): 1119–26. http://dx.doi.org/10.1039/p19920001119.

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20

Schaus, John, Joseph Krushinski, Kevin Ruley, and Vincent Rocco. "Synthesis of Homochiral 2-(2-Arylethyl)piperazines." Synthesis 2007, no. 15 (July 2007): 2307–12. http://dx.doi.org/10.1055/s-2007-983791.

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21

Sewald, Norbert, and Volkmar Wendisch. "Synthesis of homochiral camphor annulated pyrrole derivatives." Tetrahedron: Asymmetry 7, no. 5 (May 1996): 1269–72. http://dx.doi.org/10.1016/0957-4166(96)00140-1.

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22

Evans, P. Andrew, Andrew B. Holmes, and Keith Russell. "Synthesis of homochiral unsaturated seven-membered lactams." Tetrahedron: Asymmetry 1, no. 9 (January 1990): 593–96. http://dx.doi.org/10.1016/0957-4166(90)80009-n.

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23

LOHRAY, B. B., and J. R. AHUJA. "ChemInform Abstract: Synthesis of Homochiral Amino Alcohols, Aziridines, and Diamines via Homochiral Cyclic Sulfites." ChemInform 22, no. 21 (August 23, 2010): no. http://dx.doi.org/10.1002/chin.199121125.

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24

Yang, Xiu-Li, and Chuan-De Wu. "Recent advances on porous homochiral coordination polymers containing amino acid synthons." CrystEngComm 16, no. 23 (2014): 4907–18. http://dx.doi.org/10.1039/c3ce42508h.

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25

Vroemans, Robby, Sergio R. Ribone, Joice Thomas, Luc Van Meervelt, Thierry Ollevier, and Wim Dehaen. "Synthesis of homochiral sulfanyl- and sulfoxide-substituted naphthyltriazoles and study of the conformational stability." Organic & Biomolecular Chemistry 19, no. 29 (2021): 6521–26. http://dx.doi.org/10.1039/d1ob00784j.

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26

Nelson, Keith A., and Eugene A. Mash. "Homochiral ketals in organic synthesis. Enantioselective synthesis of (R)-muscone." Journal of Organic Chemistry 51, no. 14 (July 1986): 2721–24. http://dx.doi.org/10.1021/jo00364a019.

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27

Mash, Eugene A., and James A. Fryling. "Homochiral ketals in organic synthesis. Enantioselective synthesis of (+)-.beta.-eudesmol." Journal of Organic Chemistry 52, no. 14 (July 1987): 3000–3003. http://dx.doi.org/10.1021/jo00390a010.

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28

Borrego, Elena, Antonio I. Nicasio, Eleuterio Álvarez, Francisco Montilla, José Manuel Córdoba, and Agustín Galindo. "Synthesis and structural characterization of homochiral coordination polymers with imidazole-based monocarboxylate ligands." Dalton Transactions 48, no. 24 (2019): 8731–39. http://dx.doi.org/10.1039/c9dt01237k.

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29

Bělohradský, Martin, Luděk Ridvan, and Jiří Závada. "Synthesis of Homochiral Acyclic Mono- and Bis(α-amino acid)s with Oligo(oxyethylene) Chains." Collection of Czechoslovak Chemical Communications 68, no. 7 (2003): 1319–25. http://dx.doi.org/10.1135/cccc20031319.

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Synthesis of homochiral α-amino acids 3a-3e and bis(α-amino acid)s 4a-4e via BF3·Et2O-catalyzed ring-opening of methyl (S)-1-[(benzyloxy)carbonyl]aziridine-2-carboxylate (7) with oligo(ethylene glycol)s and subsequent acid hydrolysis is reported.

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30

Gartshore, Christopher J., and David W. Lupton. "Studies on the Enantioselective Synthesis of Carbazolones as Intermediates in Aspidosperma and Kopsia Alkaloid Synthesis." Australian Journal of Chemistry 66, no. 8 (2013): 882. http://dx.doi.org/10.1071/ch13287.

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Two strategies for the assembly of homochiral carbazolones have been investigated. The first exploited desymmetrisation of 1,3-cyclohexadione derivatives however this failed to deliver satisfactory outcomes. An orthogonal route exploiting palladium catalysed decarboxylative allylation of racemic carbazolone β-ketoesters has been developed. Herein we report full details on the development of this reaction and clarify apparent discrepancies between our preliminary reports and those of Shao.

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31

Wünsch, Bernhard, Matthias Zott, and Georg Höfner. "Benzomorphan analogous CNS agents: synthesis of homochiral epoxybenzocyclooctenamines." Tetrahedron 50, no. 27 (January 1994): 8003–10. http://dx.doi.org/10.1016/s0040-4020(01)85285-6.

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32

Easton, Christopher J., Craig A. Hutton, Wui Tan Eng, and Edward R. T. Tiekink. "Synthesis of homochiral hydroxy-α-amino acid derivatives." Tetrahedron Letters 31, no. 48 (January 1990): 7059–62. http://dx.doi.org/10.1016/s0040-4039(00)97242-3.

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33

Chow, Hak-Fun, Lai Fan Fok, and Chi Ching Mak. "Synthesis and characterization of optically active, homochiral dendrimers." Tetrahedron Letters 35, no. 21 (May 1994): 3547–50. http://dx.doi.org/10.1016/s0040-4039(00)73234-5.

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34

Peuchmaur, Marine, and Yung-Sing Wong. "Diastereodivergent Strategies for the Synthesis of Homochiral Aculeatins." Journal of Organic Chemistry 72, no. 14 (July 2007): 5374–79. http://dx.doi.org/10.1021/jo0707986.

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35

Tenius, Beatriz S. M., Eduardo R. de Oliveira, and Helena M. C. Ferraz. "An improved synthesis of homochiral octalones from (−)-carvone." Tetrahedron: Asymmetry 4, no. 4 (April 1993): 633–36. http://dx.doi.org/10.1016/s0957-4166(00)80166-4.

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36

Agami, Claude, Catherine Kadouri-Puchot, and Valérie Le Guen. "Synthesis of homochiral α-cyperone via enantioselective catalysis." Tetrahedron: Asymmetry 4, no. 4 (April 1993): 641–44. http://dx.doi.org/10.1016/s0957-4166(00)80168-8.

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37

Brown, Roger F. C., W. Roy Jackson, and Tom D. McCarthy. "The synthesis of homochiral naturally occurring hydroxy amides." Tetrahedron: Asymmetry 4, no. 2 (February 1993): 205–6. http://dx.doi.org/10.1016/s0957-4166(00)82338-1.

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38

Mellin-Morlière, Christelle, David J. Aitken, Steven D. Bull, Stephen G. Davies, and Henri-Philippe Husson. "A practical asymmetric synthesis of homochiral α-arylglycines." Tetrahedron: Asymmetry 12, no. 1 (February 2001): 149–55. http://dx.doi.org/10.1016/s0957-4166(01)00022-2.

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39

Roos, Gregory H. P., and M. Anthony McKervey. "A Facile Synthesis of Homochiral Rh(II) Carboxylates." Synthetic Communications 22, no. 12 (June 1992): 1751–56. http://dx.doi.org/10.1080/00397919208020494.

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40

Lesnikowski, Zbigniew J., Maria Jaworska, and Wojciech J. Stec. "Stereoselective synthesis of P-homochiral oligo(thymidine methanephosphonates)." Nucleic Acids Research 16, no. 24 (1988): 11675–89. http://dx.doi.org/10.1093/nar/16.24.11675.

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41

ABAD, A., C. AGULLO, M. ARNO, A. C. CUNAT, B. MESEGUER, and R. J. ZARAGOZA. "ChemInform Abstract: Synthesis of Homochiral Phenanthrones from Carvone." ChemInform 26, no. 14 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199514129.

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42

ALKER, D., D. N. JONES, G. M. TAYLOR, and W. W. WOOD. "ChemInform Abstract: Synthesis of Homochiral Trisubstituted γ-Butyrolactones." ChemInform 23, no. 2 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199202296.

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43

Johnson, Carl R., and Tsuneo Imamoto. "Synthesis of polydentate ligands with homochiral phosphine centers." Journal of Organic Chemistry 52, no. 11 (May 1987): 2170–74. http://dx.doi.org/10.1021/jo00387a010.

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44

Pietrusiewicz, K. M., M. Zabłocka, and W. Wisniewski. "Synthesis of Homochiral Phosphorus Compounds: the Chiron Approach." Phosphorus, Sulfur, and Silicon and the Related Elements 49-50, no. 1-4 (May 1990): 263–66. http://dx.doi.org/10.1080/10426509008038956.

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45

O’Neil, Ian A., Neil D. Miller, Jim V. Barkley, Caroline M. R. Low, and S. Barret Kalindjian. "The Synthesis of Proline Derived Homochiral Amine Oxides." Synlett 1995, no. 06 (June 1995): 617–18. http://dx.doi.org/10.1055/s-1995-5027.

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46

Zavakhina, M. S., M. P. Yutkin, D. G. Samsonenko, D. N. Dybtsev, and V. P. Fedin. "Synthesis and structure of homochiral polymeric praseodymium tartrate." Russian Chemical Bulletin 60, no. 11 (November 2011): 2425–28. http://dx.doi.org/10.1007/s11172-011-0373-7.

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47

Jiang, Zhan-Guo, Xin Wu, Zhong-Xuan Xu, Cai-Hong Zhan, and Jian Zhang. "Synthesis and photocatalytic activities of two homochiral metal–organic frameworks with cages and hydrogen bonding helices." CrystEngComm 22, no. 25 (2020): 4206–9. http://dx.doi.org/10.1039/d0ce00700e.

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48

Mash, Eugene A., and Keith A. Nelson. "Homochiral ketals in organic synthesis. Enantioselective synthesis of [m.n.1] Propellanones." Tetrahedron Letters 27, no. 13 (January 1986): 1441–44. http://dx.doi.org/10.1016/s0040-4039(00)84280-x.

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49

Li, Min-Yu, Fei Wang, Zhi-Gang Gu, and Jian Zhang. "Synthesis of homochiral zeolitic metal–organic frameworks with amino acid and tetrazolates for chiral recognition." RSC Advances 7, no. 9 (2017): 4872–75. http://dx.doi.org/10.1039/c6ra27069g.

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By mixing amino acids and tetrazolate ligands, a series of homochiral zeolitic metal–organic frameworks (ZMOFs) with ABW topology have been synthesized, which show permanent microporosity and potential enantioselective recognition ability.

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50

Cambie, RC, SE Holroyd, PS Rutledge, and PD Woodgate. "Experiments Directed Towards the Synthesis of Anthracyclinones. XVIII. Novel Dioxepins From the Boron-Trifluoride Catalyzed Cyclization of Methallyl Anthraquinone Acetals." Australian Journal of Chemistry 46, no. 5 (1993): 703. http://dx.doi.org/10.1071/ch9930703.

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