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Journal articles on the topic 'Hydrolytic kinetic resolution (HKR)'

Author: Grafiati

Published: 4 June 2021

Last updated: 9 February 2022

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1

Krishna, Palakodety, Mopuri Reddy, and Gembali Manikanta. "First Stereoselective Total Synthesis of Anti-Inflammatory Metabolite Penicillinolide A." Synthesis 51, no. 06 (2018): 1427–34. http://dx.doi.org/10.1055/s-0037-1611040.

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The first asymmetric total synthesis of penicillinolide A is described. Key steps of the synthesis involve Jacobsen’s hydrolytic kinetic resolution (HKR), chelation controlled allylation, Brown’s asymmetric allylation, hydroboration, and Yamaguchi lactonization.

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2

Pemha, René, Dieudonné Emmanuel Pegnyemb, and Paul Mosset. "Synthesis of (2S,3R,5R)-2-Azido-3,5-dihydroxynonadecane Sphingolipid Analogue." Synthesis 52, no. 17 (2020): 2572–78. http://dx.doi.org/10.1055/s-0040-1707397.

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A concise and highly efficient synthesis of an enigmol analogue has been achieved. The synthetic strategy features Jacobsen’s hydrolytic kinetic resolution (HKR) and epoxide opening by alkynyl boranes as the key steps.

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3

Kumar, Pradeep, Vasudeva Naidu, and Priti Gupta. "Application of hydrolytic kinetic resolution (HKR) in the synthesis of bioactive compounds." Tetrahedron 63, no. 13 (2007): 2745–85. http://dx.doi.org/10.1016/j.tet.2006.12.015.

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4

Yang, Yun-Xu, and Shi-Xiang Liu. "Asymmetric-Catalysed Preparation and Stereochemistry of (R,R)-,(S,R)-(6-Fluoro-2-Chromanyl)-1,2-Ethanediol." Journal of Chemical Research 2007, no. 9 (2007): 506–8. http://dx.doi.org/10.3184/030823407x240908.

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(R,R)-,(S,R)-1-(6-fluoro-2-chromanyl)-1,2-ethanediol 1a/1b were prepared by hydrolytic kinetic resolution (HKR) of terminal racemic epoxides using (R,R)-SalenCo(OAc) as a catalyst. Their configurations were established by comparison with two authentic samples by HPLC.

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5

Kureshy, R. I., N. H. Khan, S. H. R. Abdi, S. T. Patel, and R. V. Jasra. "Simultaneous production of chirally enriched epoxides and 1,2-diols from racemic epoxides via hydrolytic kinetic resolution (HKR)." Journal of Molecular Catalysis A: Chemical 179, no. 1-2 (2002): 73–77. http://dx.doi.org/10.1016/s1381-1169(01)00394-6.

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6

Rossbach, Benjamin M., Kerstin Leopold, and Ralf Weberskirch. "Self-Assembled Nanoreactors as Highly Active Catalysts in the Hydrolytic Kinetic Resolution (HKR) of Epoxides in Water." Angewandte Chemie International Edition 45, no. 8 (2006): 1309–12. http://dx.doi.org/10.1002/anie.200503291.

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7

Aerts, Sven, Anita Buekenhoudt, Herman Weyten, Ivo F. J. Vankelecom, and Pierre A. Jacobs. "The influence of solvent choice, acid activation and surfactant addition on the hydrolytic kinetic resolution (HKR) of terminal epoxides." Tetrahedron: Asymmetry 16, no. 3 (2005): 657–60. http://dx.doi.org/10.1016/j.tetasy.2004.11.024.

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8

Roy, Tamal, Sunirmal Barik, Manish Kumar, et al. "Asymmetric hydrolytic kinetic resolution with recyclable polymeric Co(iii)–salen complexes: a practical strategy in the preparation of (S)-metoprolol, (S)-toliprolol and (S)-alprenolol: computational rationale for enantioselectivity." Catal. Sci. Technol. 4, no. 11 (2014): 3899–908. http://dx.doi.org/10.1039/c4cy00594e.

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9

Aerts, S., A. Buekenhoudt, H. Weyten, L. E. M. Gevers, I. F. J. Vankelecom, and P. A. Jacobs. "The use of solvent resistant nanofiltration in the recycling of the Co-Jacobsen catalyst in the hydrolytic kinetic resolution (HKR) of epoxides." Journal of Membrane Science 280, no. 1-2 (2006): 245–52. http://dx.doi.org/10.1016/j.memsci.2006.01.025.

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10

Key, Rebecca E., Krishnan Venkatasubbaiah, and Christopher W. Jones. "Evaluation of enantiopure and non-enantiopure Co(III)-salen catalysts and their counter-ion effects in the hydrolytic kinetic resolution (HKR) of racemic epichlorohydrin." Journal of Molecular Catalysis A: Chemical 366 (January 2013): 1–7. http://dx.doi.org/10.1016/j.molcata.2012.08.013.

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11

Dijk, Ewold W., Ben L. Feringa, and Gerard Roelfes. "DNA-based hydrolytic kinetic resolution of epoxides." Tetrahedron: Asymmetry 19, no. 20 (2008): 2374–77. http://dx.doi.org/10.1016/j.tetasy.2008.10.004.

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12

Kondekar, Nagendra B., and Pradeep Kumar. "Synthesis of (R)-Selegiline via Hydrolytic Kinetic Resolution." Synthetic Communications 41, no. 9 (2011): 1301–8. http://dx.doi.org/10.1080/00397911.2010.481751.

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13

Shepperson, Ian, Marco Cavazzini, Gianluca Pozzi, and Silvio Quici. "Fluorous biphasic hydrolytic kinetic resolution of terminal epoxides." Journal of Fluorine Chemistry 125, no. 2 (2004): 175–80. http://dx.doi.org/10.1016/j.jfluchem.2003.07.008.

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14

Gupta, Priti, S. Vasudeva Naidu, and Pradeep Kumar. "Enantioselective synthesis of tarchonanthuslactone via iterative hydrolytic kinetic resolution." Tetrahedron Letters 46, no. 38 (2005): 6571–73. http://dx.doi.org/10.1016/j.tetlet.2005.07.056.

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15

Kiełbasiński, Piotr, Binne Zwanenburg, Theodorus J. G. Damen, Michał W. Wieczorek, Wiesław R. Majzner, and Grzegorz D. Bujacz. "Kinetic Resolution of Racemic Cyclic Sulfoxides Using Hydrolytic Enzymes." European Journal of Organic Chemistry 1999, no. 10 (1999): 2573–78. http://dx.doi.org/10.1002/(sici)1099-0690(199910)1999:10<2573::aid-ejoc2573>3.0.co;2-g.

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16

Weck, M., P. Goyal, and X. Zheng. "Hydrolytic Kinetic Resolution with Resin-Supported Co-(Salen) Catalysts." Synfacts 2008, no. 11 (2008): 1235. http://dx.doi.org/10.1055/s-0028-1083406.

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17

Bredihhina, Jevgenia, Piret Villo, Ka̅rlis Andersons, Lauri Toom, and Lauri Vares. "Hydrolytic and Aminolytic Kinetic Resolution of Terminal Bis-Epoxides." Journal of Organic Chemistry 78, no. 6 (2013): 2379–85. http://dx.doi.org/10.1021/jo3024335.

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18

Gupta, Priti, S. Vasudeva Naidu, and Pradeep Kumar. "A practical enantioselective synthesis of massoialactone via hydrolytic kinetic resolution." Tetrahedron Letters 45, no. 4 (2004): 849–51. http://dx.doi.org/10.1016/j.tetlet.2003.11.032.

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19

Narsaiah, A. Venkat, and J. Kranthi Kumar. "Novel Asymmetric Synthesis of (S)-Esmolol Using Hydrolytic Kinetic Resolution." Synthetic Communications 41, no. 11 (2011): 1603–8. http://dx.doi.org/10.1080/00397911.2010.488495.

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20

Kondekar, Nagendra B., and Pradeep Kumar. "ChemInform Abstract: Synthesis of (R)-Selegiline via Hydrolytic Kinetic Resolution." ChemInform 42, no. 41 (2011): no. http://dx.doi.org/10.1002/chin.201141053.

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21

Kielbasinski, Piotr, Binne Zwanenburg, Theodorus J. G. Damen, Michal W. Wieczorek, Wieslaw R. Majzner, and Grzegorz D. Bujacz. "ChemInform Abstract: Kinetic Resolution of Racemic Cyclic Sulfoxides Using Hydrolytic Enzymes." ChemInform 31, no. 2 (2010): no. http://dx.doi.org/10.1002/chin.200002051.

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22

Zhu, Chengfeng, Guozan Yuan, Xu Chen, Zhiwei Yang, and Yong Cui. "Chiral Nanoporous Metal–Metallosalen Frameworks for Hydrolytic Kinetic Resolution of Epoxides." Journal of the American Chemical Society 134, no. 19 (2012): 8058–61. http://dx.doi.org/10.1021/ja302340b.

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23

Kumar, Pradeep, and Anand Harbindu. "Synthesis of Aculeatins A and B via Iterative Hydrolytic Kinetic Resolution." Synthesis 2010, no. 09 (2010): 1479–84. http://dx.doi.org/10.1055/s-0029-1218687.

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24

Subhas Bose, D., and A. Venkat Narsaiah. "An efficient asymmetric synthesis of (S)-atenolol: using hydrolytic kinetic resolution." Bioorganic & Medicinal Chemistry 13, no. 3 (2005): 627–30. http://dx.doi.org/10.1016/j.bmc.2004.10.057.

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25

Blechschmidt, Daniel R., Matthew D. Woodhouse, Sebastien Inagaki, et al. "Aromatic donor–acceptor interaction promoted catalyst assemblies for hydrolytic kinetic resolution of epichlorohydrin." Organic & Biomolecular Chemistry 17, no. 1 (2019): 172–80. http://dx.doi.org/10.1039/c8ob02249f.

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26

Mujahid, Mohammad, Jambu Subramanian, Viswanadh Nalla, Murugesan Sasikumar, Sunita Sharad Kunte, and Murugan Muthukrishnan. "A new and efficient enantioselective synthesis of both enantiomers of the calcium channel blocker bepridil." New Journal of Chemistry 41, no. 2 (2017): 824–29. http://dx.doi.org/10.1039/c6nj02928k.

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27

Zhu, Xunjin, Krishnan Venkatasubbaiah, Marcus Weck, and Christopher W. Jones. "Kinetic Evaluation of Cooperative [Co(salen)] Catalysts in the Hydrolytic Kinetic Resolution of rac-Epichlorohydrin." ChemCatChem 2, no. 10 (2010): 1252–59. http://dx.doi.org/10.1002/cctc.201000162.

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28

Krishnamurthy, Suvratha, Jalli Venkataprasad, Tarun Chand Vagvala, Tetsuji Moriguchi та Akihiko Tsuge. "α-Chymotrypsin andl-acylase aided synthesis of 5-hydroxypipecolic acid via Jacobsen's hydrolytic kinetic resolution of epoxy amino acids". RSC Advances 5, № 64 (2015): 52154–60. http://dx.doi.org/10.1039/c5ra09207h.

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5-hydroxypipecolic acid synthesis from intramolecular reaction of epoxy amino acids; enantiomers separated by hydrolase and diastereomeric epoxide separated by Jacobsen's hydrolytic kinetic resolution.

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29

Dubey, Abhishek, Shruti V. Kauloorkar, and Pradeep Kumar. "Synthesis of (−)-galantinic acid via iterative hydrolytic kinetic resolution and tethered aminohydroxylation." Tetrahedron 66, no. 17 (2010): 3159–64. http://dx.doi.org/10.1016/j.tet.2010.02.093.

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30

Hong, Xiang, Mohamed Mellah, and Emmanuelle Schulz. "Heterobimetallic dual-catalyst systems for the hydrolytic kinetic resolution of terminal epoxides." Catalysis Science & Technology 4, no. 8 (2014): 2608. http://dx.doi.org/10.1039/c4cy00235k.

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31

Narsaiah, A. Venkat, and J. Kranthi Kumar. "ChemInform Abstract: Novel Asymmetric Synthesis of (S)-Esmolol Using Hydrolytic Kinetic Resolution." ChemInform 42, no. 44 (2011): no. http://dx.doi.org/10.1002/chin.201144062.

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32

Gurjar, M. K., B. V. N. B. S. Sarma, K. Sadalapure, and S. Adhikari. "A Practical Synthesis of (R)- and (S)-Benzylglycidols by Hydrolytic Kinetic Resolution." Synthesis 1998, no. 10 (1998): 1424. http://dx.doi.org/10.1055/s-1998-2179.

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33

Chun, Byeong Jae, Jie Lu, Marcus Weck, and Seung Soon Jang. "Characterization of molecular association of poly(2-oxazoline)s-based micelles with various epoxides and diols via the Flory–Huggins theory: a molecular dynamics simulation approach." Physical Chemistry Chemical Physics 17, no. 43 (2015): 29161–70. http://dx.doi.org/10.1039/c5cp03854e.

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The hydrolytic kinetic resolution of epoxides has been performed in a shell-crosslinked micellar consisting of amphiphilic triblock copolymers based on poly(2-oxazline)s with Co(iii)-salens at the micelle core.

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34

Ghotekar, Ganesh S., Devidas A. More, Viswanadh Nalla, and M. Muthukrishnan. "A new enantioselective synthesis of antiobesity drug lorcaserin." New Journal of Chemistry 43, no. 43 (2019): 16876–80. http://dx.doi.org/10.1039/c9nj04234b.

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A simple and efficient enantioselective synthesis of anti-obesity drug lorcaerin starting from easily accessible 3-chlorostyrene oxide has been described for the first time employing hydrolytic kinetic resolution as a source of chirality.

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35

Sasikumar, Murugesan, Milind D. Nikalje, and Murugan Muthukrishnan. "A convenient synthesis of enantiomerically pure (R)-mexiletine using hydrolytic kinetic resolution method." Tetrahedron: Asymmetry 20, no. 24 (2009): 2814–17. http://dx.doi.org/10.1016/j.tetasy.2009.11.014.

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36

Kang, Byungman, and Sukbok Chang. "A facile synthetic route to (+)-allosedamine via hydrolytic kinetic resolution and olefin metathesis." Tetrahedron 60, no. 34 (2004): 7353–59. http://dx.doi.org/10.1016/j.tet.2004.05.054.

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37

Yu, Qian, Yikang Wu, Li-Jun Xia, Min-Hua Tang, and Yu-Lin Wu. "Synthesis of a key intermediate for corossolin using hydrolytic kinetic resolution of epoxides." Chemical Communications, no. 2 (1999): 129–30. http://dx.doi.org/10.1039/a808923j.

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38

Kumar, Pradeep, and Priti Gupta. "Hydrolytic Kinetic Resolution as an Emerging Tool in the Synthesis of Bioactive Molecules." Synlett 2009, no. 09 (2009): 1367–82. http://dx.doi.org/10.1055/s-0029-1217171.

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39

Furrow, Michael E., Scott E. Schaus, and Eric N. Jacobsen. "Practical Access to Highly Enantioenriched C-3 Building Blocks via Hydrolytic Kinetic Resolution." Journal of Organic Chemistry 63, no. 20 (1998): 6776–77. http://dx.doi.org/10.1021/jo981332d.

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40

Cavazzini, Marco, Silvio Quici, and Gianluca Pozzi. "Hydrolytic kinetic resolution of terminal epoxides catalyzed by fluorous chiral Co(salen) complexes." Tetrahedron 58, no. 20 (2002): 3943–49. http://dx.doi.org/10.1016/s0040-4020(02)00216-8.

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41

Zheng, Xiaolai, Christopher W Jones, and Marcus Weck. "Engineering Polymer-Enhanced Bimetallic Cooperative Interactions in the Hydrolytic Kinetic Resolution of Epoxides." Advanced Synthesis & Catalysis 350, no. 2 (2008): 255–61. http://dx.doi.org/10.1002/adsc.200700339.

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42

Kahn, Michael G. C., and Marcus Weck. "Highly crosslinked polycyclooctyl-salen cobalt (iii) for the hydrolytic kinetic resolution of terminal epoxides." Catal. Sci. Technol. 2, no. 2 (2012): 386–89. http://dx.doi.org/10.1039/c1cy00290b.

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43

Muthukrishnan, M., Dinesh R. Garud, R. R. Joshi та R. A. Joshi. "Concise synthesis of β-blockers (S)-metoprolol and (S)-betaxolol using hydrolytic kinetic resolution". Tetrahedron 63, № 8 (2007): 1872–76. http://dx.doi.org/10.1016/j.tet.2006.12.016.

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44

Rim Oh, Chun, Dong Joon Choo, Woo Ho Shim, et al. "Chiral Co(iii)(salen)-catalysed hydrolytic kinetic resolution of racemic epoxides in ionic liquids." Chemical Communications, no. 9 (April 2, 2003): 1100–1101. http://dx.doi.org/10.1039/b301490h.

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45

Kawthekar, Rahul B., and Geon‐Joong Kim. "Hydrolytic Kinetic Resolution of Terminal Epoxides catalyzed by Novel Bimetallic Chiral Co (Salen) Complexes." Synthetic Communications 38, no. 8 (2008): 1236–48. http://dx.doi.org/10.1080/00397910701872658.

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46

Radha Krishna, Palakodety, and V. V. Ramana Reddy. "Stereoselective total synthesis of (+)-cryptocarya diacetate by an iterative Jacobsen’s hydrolytic kinetic resolution protocol." Tetrahedron Letters 46, no. 22 (2005): 3905–7. http://dx.doi.org/10.1016/j.tetlet.2005.03.202.

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47

Brandes, Bridget D., and Eric N. Jacobsen. "Synthesis of enantiopure 3-chlorostyrene oxide via an asymmetric epoxidation-hydrolytic kinetic resolution sequence." Tetrahedron: Asymmetry 8, no. 23 (1997): 3927–33. http://dx.doi.org/10.1016/s0957-4166(97)00568-5.

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48

Li, Le, Benhua Huang, Yu Li, et al. "Macroporous Helical Silica Immobilizing Cobalt-Salen Complex Catalyzed Asymmetric Hydrolytic Kinetic Resolution of Epoxides." Catalysis Surveys from Asia 19, no. 4 (2015): 236–48. http://dx.doi.org/10.1007/s10563-015-9198-y.

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49

Bhangare, D. N., V. B. Mahale, R. G. Shinde, M. D. Nikalje, S. D. Duthade, and M. N. Lokhande. "Synthesis of the Neurokinin 1 Receptor Antagonist (+)-L-733,060 by Jacobsen’s Hydrolytic Kinetic Resolution." Russian Journal of Organic Chemistry 56, no. 12 (2020): 2159–64. http://dx.doi.org/10.1134/s1070428020120180.

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50

Dandachi, Hiba, Houssein Nasrallah, Farah Ibrahim, et al. "Chiral calix-salen cobalt complexes, catalysts for the enantioselective dynamic hydrolytic kinetic resolution of epibromohydrin." Journal of Molecular Catalysis A: Chemical 395 (December 2014): 457–62. http://dx.doi.org/10.1016/j.molcata.2014.09.012.

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