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Comments on Inorganic Chemistry
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Research Article

Recent Advancements in the Development of Osmium Catalysts for Various Oxidation Reactions: A New Era?

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References

  • Nativi, C.; Roelens, S. In Science of Synthesis, L36; J. Clayden (Ed.); 7.1 Product Subclass 1: 1,2-Diols: Thieme: Stuttgart, 2008; pp 757–762.
  • Sundermeier, U.; Döbler, C.; Beller, M. In Modern Oxidation Methods; J.-E. Bäckvall (Ed.); Recent Developments in the Osmium-Catalyzed Dihydroxylation of Olefins; Wiley-VCH: Weinheim, 2004; pp 1–20.
  • Heitbaum, M.; Glorius, F.; Escher, I. Asymmetric Heterogeneous catalysis. Angew.Chem. Int. Ed. 2006, 45, 4732.
  • Schroeder, M.;. Osmium Tetraoxide Cis Hydroxylation of Unsaturated Substrates. Chem. Rev. 1980, 80(2), 187–213. DOI: https://doi.org/10.1021/cr60324a003.
  • Wang, Z.-M.; Sharpless, K. B. A Solid-to-Solid Asymmetric Dihydroxylation Procedure for Kilogram-Scale Preparation of Enantiopure Hydrobenzoin. J. Org. Chem. 1994, 59(26), 8302–8303. DOI: https://doi.org/10.1021/jo00105a065.
  • Song, C. E.; Yang, J. W.; Ha, H. J.; Lee, S.-G. Efficient and Practical Polymeric Catalysts for Heterogeneous Asymmetric Dihydroxylation of Olefins. Tetrahedron: Asymmetry. 1996, 7(3), 645–648. DOI: https://doi.org/10.1016/0957-4166(96)00054-7.
  • Han, H.; Janda, K. D. Multipolymer-Supported Substrate and Ligand Approach to the Sharpless Asymmetric Dihydroxylation. Angew. Chem. Int. Ed. 1997, 36(16), 1731–1733. DOI: https://doi.org/10.1002/anie.199717311.
  • Lee, B. S.; Mahajan, S.; Janda, K. D. Asymmetric Dihydroxylation Catalyzed by Ionic Polymer-supported Osmium Tetroxide. Tetrahedron Lett. 2005, 46(26), 4491–4493. DOI: https://doi.org/10.1016/j.tetlet.2005.04.113.
  • (a) Fujita, M.; Costas, M.; Que, L., Jr. Iron-catalyzed Olefin Cis-dihydroxylation by H2O2: Electrophilic versus Nucleophilic Mechanisms. J. Am. Chem. Soc. 2003, 125(33), 9912–9913. DOI: https://doi.org/10.1021/ja029863d. (b) Suzuki, K.; Oldenbug, P.D.; Que, L.; Jr. Angew. Chem. 2008, 120, 1913 – 1915 (c) Bruijnincx, P.C.A.; Buurmans, I.L.C.; Gosiewska, S.; Moelands, M.A.H.; Lutz, M.; Spek, A.L.; Koten, G.; Gebbink, R.J.M.K.; Chem. Eur. J. 2008, 14, 1228 – 1237.
  • (a) De Boer, J. W.; Brinksma, J.; Browne, W. R.; Meetsma, A.; Alsters, P. L.; Hage, R.; Feringa, B. L. cis-Dihydroxylation and Epoxidation of Alkenes by [Mn2o (RCO2) 2 (Tmtacn) 2]: Tailoring the Selectivity of a Highly H2O2-efficient Catalyst. J. Am. Chem. Soc. 2005, 127(22), 7990–7991. DOI: https://doi.org/10.1021/ja050990u. b) Chow, T. W.-S.; Yungen, L.; Che, C.-M.; Chem. Commun. 2011, 47, 11204 –11206.
  • Yip, W.-P.; Ho, C.-M.; Zhu, N.; Lau, T.-C.; Che, C.-M. Homogeneous [Ruiii(me3tacn)cl3]-catalyzed Alkenecis-Dihydroxylation with Aqueous Hydrogen Peroxide. Chem. Asian J. 2008, 3(1), 70–77. DOI: https://doi.org/10.1002/asia.200700237.
  • (a) Kolb, H. C.; Van Nieuwenhze, M. S.; Sharpless, K. B. Catalytic Asymmetric Dihydroxylation. Chem. Rev. 1994, 94(8), 2483–2547. DOI: https://doi.org/10.1021/cr00032a009. (b) Andersson, M. A.; Epple, R.; Fokin, V. V.; Sharpless, K.B. Angew. Chem., Int. Ed. 2002, 41, 472–475.
  • (a) De Vos, D. E.; Sels, B. F.; Jacobs, P. A. Immobilization of homogeneous oxidation catalysts. Adv. Catal. 2002,46, 1. (b) Severeyns, A.; De Vos, D.E.; Jacobs, P.A. Towards Heterogeneous and Green Versions of Os Dihydroxylation Catalysis. Top. Catal. 2002, 19, 125.
  • Bolm, C.; Maischak, A.; Gerlach, A. Asymmetric Dihydroxylation with Silica-anchored Alkaloids. Chem. Commun. 1997, 24, 2353–2354. DOI: https://doi.org/10.1039/a706605h.
  • (a) Pini, D.; Petri, A.; Nardi, A.; Rosini, C.; Salvadori, P. Heterogeneous Catalytic Asymmetric Dihydroxylation of Olefins with the OsO4/Poly(9--Acylquinine-co-Acrylonitrile) System. Tetrahedron Lett. 1991, 32(38), 5175. DOI: https://doi.org/10.1016/S0040-4039(00)93459-2. (b) Salvatori, P.; Pini, D.; Petri, A. J. Am. Chem. Soc., 1997, 119, 6929 (c) Bolm, C.; Gerlach, A.; Eur. J. Org. Chem. 1998, 21.
  • Motorina, I.; Crudden, C. M. Asymmetric Dihydroxylation of Olefins Using Cinchona Alkaloids on Highly Ordered Inorganic Supports. Org. Lett. 2001, 3(15), 2325. DOI: https://doi.org/10.1021/ol010096h.
  • Herrmann, W. A.; Kratzer, R. M.; Blumel, J.; Friedrich, H. B.; Fischer, R. W.; Apperley, D. C.; Mink, J.; Berkesi, O. Polymer-bound Osmium Oxide Catalysts. J. Mol. Catal. A. 1997, 120(1–3), 197–205. DOI: https://doi.org/10.1016/S1381-1169(96)00419-0.
  • (a) Kim, B. M.; Sharpless, K. B. Heterogeneous Catalytic Asymmetric Dihydroxylation: Use of a Polymer-bound Alkaloid. Tetrahedron Lett. 1990, 31(21), 3003. DOI: https://doi.org/10.1016/S0040-4039(00)89009-7. (b) Lohray, B.B.; Thomas, A.; Chittari, P.; Ahuja, J. R.; Dhal, P. K. Tetrahedron Lett. 1992, 33, 5453. (c) Han, H.; Janda, K.D.; J. Am. Chem. Soc. 1996, 118, 7632. (d) Bolm, C.; Gerlach, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 741.
  • (a) Nagayama, S.; Endo, M.; Kobayashi, S. Microencapsulated Osmium Tetraoxide. A New Recoverable and Reusable Polymer-Supported Osmium Catalyst for Dihydroxylation of Olefins. J. Org. Chem. 1998, 63(18), 6094. DOI: https://doi.org/10.1021/jo981127y. (b) Kobayashi, S.; Endo M.; Nagayama, S. J. Am. Chem. Soc. 1999, 121, 11229; (c) Choudary, B.M.; Chowdari, N.S.; Jyothi, K.; Kantam, M.L. J. Am. Chem. Soc. 2002, 124, 5341; (d) Choudary, B.M.; Jyothi, K.; Madhi, S.; Kantam, M.L. Adv. Synth. Catal. 2003, 345, 1190; (e) Kobayashi, S.; Akiyama, R. Chem. Commun. 2003, 449.
  • Kobayashi, S.; Sugiura, M. Immobilization of Osmium Catalysts for Asymmetric Dihydroxylation of Olefins. Adv. Synth. Catal. 2006, 348(12–13), 1496. DOI: https://doi.org/10.1002/adsc.200606210.
  • Lazarus, L. L.; Brutchey, R. L. Heterogeneous Fullerene-supported Osmium Tetroxide Catalyst for the Cis-dihydroxylation of Olefins. Dalton Trans. 2010, 39(34), 7888–7890. DOI: https://doi.org/10.1039/c0dt00599a.
  • Van Rheenen, V.; Kelly, R. C.; Cha, D. Y. An Improved Catalytic OsO4 Oxidation of Olefins to −1,2-glycols Using Tertiary Amine Oxides as the Oxidant. Tetrahedron Lett. 1976, 17(23), 1973. DOI: https://doi.org/10.1016/S0040-4039(00)78093-2.
  • Goswami, T. H.; Singh, R. In Fullerene Research Advances, 1st ed.; Kramer, C. N., Ed.; Recent Development of Fullerenol Research. Nova Science Publishers: New York, 2007; ch. 3, pp 55–69.
  • (a) Fortner, J. D.; Kim, D.; Boyd, A. M.; Faulkner, J. C.; Moran, S.; Colvin, V. L.; Hughes, J. B.; Kim, J. Reaction of Water-stable C60 Aggregates with Ozone. Environ. Sci. Technol. 2007, 41(21), 7497. DOI: https://doi.org/10.1021/es0708058. (b) Chiang, L.Y.; Swirczewaki, J.W.; Hsu, C.S.; Chowdury, S.K.; Cameron, S.; Creegan, K.; J. Chem. Soc., Chem. Commun. 1992, 1791; (c) Cataldo, F.; Heymann, D.; Polym. Degrad. Stab. 2000, 70, 237; (d) Cataldo, F.; Carbon 2002, 40, 1457; (e) Vassallo, A.M.; Pang, L.S.K.; Cole-Clarke, P.A.; Wilson, M.A.; J. Am. Chem. Soc. 1991,113, 7820; (f) Xing, G.; Zhang, J.; Zhao, Y.; Tang, B. Zhang, J.; Gao, X.; Yuan, H.; Qu, L.; Cao, W.; Chai, Z.; Ibrahim, K.; Su, R.; J. Phys. Chem. B 2004,108, 11473.
  • Ogrin, D.; Barron, A. R. Highly oxygenated fullerenes by catalytic epoxidation of C60 and single walled carbon nanotubes with methyltrioxorhenium-hydrogen peroxide. J. Mol. Catal. A: Chem. 2006, 244, 267–270.
  • (a) Fujita, K.; Yamazaki, M.; Ainoya, T.; Tsuchimoto, T.; Yasuda, H. A Recyclable Dendritic Osmium Catalyst for Homogeneous Dihydroxylation of Olefins. Tetrahedron.2010, 66(44), 8536–8543. (b) Fujita, K.; Ainoya, T.; Tsuchimoto, T.; Yasuda, H. Tetrahedron Lett. 2010, 51, 808–810.
  • (a) Benito, J. M.; de Jesús, E.; de la Mata, F. J.; Flores, J. C.; Gómez, R. Generation Effects on the Microstructure and Product Distribution in Ethylene Polymerization Promoted by Dendritic Nickel Catalysts. Chem. Commun. 41, 2005, 5217–5219. DOI:https://doi.org/10.1039/b511379m. (b) Fujita, K.; Muraki, T.; Sakurai, T.; Oishi, A.; Taguchi, Y. Chem. Lett. 2005, 34, 1180– 1181; (c) Muraki, T.; Fujita, K.; Oishi, A.; Taguchi, Y. Polym. J. 2005, 37, 847–853; (d) Ribourdouille, Y.; Engel, G. D.; Richard-Plouet, M.; Gade, L.H. Chem.Commun. 2003, 1228–1229; (e) Mizugaki, T.; Murata, M.; Ooe, M.; Ebitani, K.;Kaneda, K. Chem. Commun. 2002, 52–53.
  • (a) Snelders, D. J. M.; van Koten, G.; Gebbink, R. J. M. K. Hexacationic Dendriphos Ligands in the Pd-Catalyzed Suzuki−Miyaura Cross-Coupling Reaction: Scope and Mechanistic Studies. J. Am. Chem. Soc. 2009, 131(32), 11407–11416. DOI: https://doi.org/10.1021/ja904042h. (b) Muraki, T.; Fujita, K.; Kujime, M. J. Org. Chem. 2007, 72, 7863–7870; (c) Hattori, H.; Fujita, K.; Muraki, T.; Sakaba, A. Tetrahedron Lett. 2007, 48, 6817–6820; (d) Wang, Z.-J.;Deng, G.-J.; Li, Y.; He, Y.-M.; Tang, W.-J.; Fan, Q.-H. Org. Lett. 2007, 9, 1243–1246; (e) Fujita, K.; Muraki, T.; Hattori, H.; Sakakura, T. Tetrahedron Lett. 2006, 47, 4831–4843; (f) Muraki, T.; Fujita, K.; Terakado, D. Synlett 2006, 2646–2648.
  • Fujita, K.; Yamazaki, M.; Ainoya, T.; Tsuchimoto, T.; Yasuda, H. A Recyclable Dendritic Osmium Catalyst for Homogeneous Dihydroxylation of Olefins. Tetrahedron. 2010, 66(44), 8536–8543. DOI: https://doi.org/10.1016/j.tet.2010.08.062.
  • Fujita, K.; Ainoya, T.; Tsuchimoto, T.; Yasuda, H. Homogeneous Dihydroxylation of Olefins Catalyzed by a Recyclable Core Dendrimer. Tetrahedron Lett. 2010, 51(5), 808–810. DOI: https://doi.org/10.1016/j.tetlet.2009.11.126.
  • Fujita, K.; Umeki, S.; Yamazaki, M.; Ainoya, T.; Tsuchimoto, T. Magnetically recoverable osmium catalysts for dihydroxylation of olefins. Tetrahedron Lett. 2011, 52, 3137–3140.
  • Severeyns, A.; De Vos, D. E.; Fiermans, L.; Verpoort, F.; Grobet, P. J.; Jacobs, P. A. A Heterogeneous cis-Dihydroxylation Catalyst with Stable, Site-Isolated Osmium-Diolate Reaction Centers. Angew. Chem. Int. Ed. 2001, 40(3), 586–589. DOI: https://doi.org/10.1002/1521-3773(20010202)40:3<586::AID-ANIE586>3.0.CO;2-L.
  • Fujita, K.-L.; Umeki, S.; Yasuda, H. Magnetically Recoverable Osmium Catalysts with Osmium-Diolate Esters for Dihydroxylation of Olefins. Synlett. 2013, 24(8), 947–950. DOI: https://doi.org/10.1055/s-0032-1316910.
  • (a) Cano, R.; Pérez, J. M.; Ramón, D. J. Osmium Impregnated on Magnetite as a Heterogeneous Catalyst for the Syn-dihydroxylation of Alkenes. Appl. Catal. A. 2014, 470, 177–182. DOI: https://doi.org/10.1016/j.apcata.2013.10.050. (b) Singh, H. S. In Organic Synthesis by Oxidation with Metal Compounds; Mijs, W. J., De Jonge, C. R. H. I., Eds.; Plenum: New York, 1986; Chapter 12. (c) Haines, A. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; 437. (d) Lohray, B.B. Tetrahedron: Asymmetry 1992, 3, 1317. (e) Johnson, R.A.; Sharpless, K.B. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993.
  • (a) Samanta, S.; Laha, S. C.; Mal, N. K.; Bhaumik, A. Co(III)-containing Mesoporous Silica as an Efficient Catalyst in Selective Dihydroxylation of Cyclohexene. J. Mol. Catal. A: Chem. 2004, 222(1–2), 235. DOI: https://doi.org/10.1016/j.molcata.2004.08.014. (b) Bhaumik, A.; Tatsumi, T. J. Catal. 1998, 176, 305.
  • Metin, Ö.; Alcan Alp, N.; Akbayrak, S.; Biçer, A.; Gültekin, M. S.; Özkarb, S.; Bozkaya, U. Dihydroxylation of Olefins Catalyzed by Zeolite-confined Osmium(0) Nanoclusters: An Efficient and Reusable Method for the Preparation of 1,2-cis-diols. Green Chem. 2012, 14(5), 1488. DOI: https://doi.org/10.1039/c2gc16616j.
  • Alp, C.; Atmaca, U.; Celik, M.; Gültekin, M. S. One-Pot Synthesis of 1,2,3-Triols from Allylic Hydroperoxides and a Catalytic Amount of OsO4 in Aqueous Acetone. Synlett. 2009, 17, 2765–2768.
  • Göksu, H.; Dalmizraka, D.; Akbayrak, S.; Gültekin, M. S.; Özkar, S.; Metin, Ö. One-pot Synthesis of 1,2/3-triols from the Allylic Hydroperoxides Catalyzed by Zeolite-confined Osmium(0) Nanoclusters. J. Mol. Catal. A: Chem. 2013, 378, 142–147. DOI: https://doi.org/10.1016/j.molcata.2013.06.013.
  • Caps, V.; Paraskevas, I.; Tsang, S. C. A Surface and Catalytic Study of Heterogenised Os3(CO)12 Species in MCM-41 Structures. Appl. Catal. A Gen. 2003, 252(1), 37–49. DOI: https://doi.org/10.1016/S0926-860X(03)00372-7.
  • Matsumoto, A.; Chen, H.; Tsutsumi, K.; Gru¨n, M.; Unger, K. Novel Route in the Synthesis of MCM-41 Containing Framework Aluminum and Its Characterization. Microporous Mesoporous Mater. 1999, 32(1–2), 55. DOI: https://doi.org/10.1016/S1387-1811(99)00089-X.
  • Kwong, H.-L.; Sorato, C.; Ogino, Y.; Chen, H.; Sharpless, K. B. Preclusion of the “Second Cycle” in the Osmium-catalyzed Asymmetric Dihydroxylation of Olefins Leads to a Superior Process. Tetrahedron Lett. 1990, 31(21), 2999. DOI: https://doi.org/10.1016/S0040-4039(00)89008-5.
  • Song, C. E.;. Enantioselective Chemo- and Bio-catalysis in Ionic Liquids. Chem. Commun. 2004, 9, 1033–1043. DOI: https://doi.org/10.1039/b309027b.
  • (a) Johnson, B. F. G.; Raynor, S. A.; Shephard, D. S.; Mashmeyer, T.; Thomas, J. M.; Sankar, G.; Bromley, S.; Oldroyd, R.; Gladden, L.; Mantlec, M. D. Superior Performance of a Chiral Catalyst Confined within Mesoporous Silica. Chem. Commun. 13, 1999, 1167. DOI:https://doi.org/10.1039/a902441g. (b) Thomas, J.M.; Maschmeyer, T.; Johnson, B.F.G.; Shephard, D.S.; J. Mol. Catal. A: Chem. 1999, 141, 139. (c) Raynor, S.A.; Thomas, J.M.; Raja, R.; Johnson, B.F.G.; Bell, R.G.; Mantlec, M.D.; Chem. Commun. 2000, 1925 (d) Raja, R.; Thomas, J.M.; Jones, M.D.; Johnson, B.F.G.; Vaughan, D.E.W.; J. Am. Chem. Soc. 2003, 125, 14982 (e) Jones, M.D.; Raja, R.; Thomas, J.M.; Johnson, B.F.G.; Lewis, D.W.; Rouzaud, J.; Harris, K.D.M.; Angew. Chem., Int. Ed. 2003, 42, 4326.
  • Caps, V.; Paraskevas, I.; Tsang, S. C. Unexpectedly superior enantioselectivity for trans-stilbenecis-dihydroxylation over anchored triosmium carbonyl species inconfined Al-MCM-41 channels. Chem. Commun. 2005, 1781–1783.
  • Matsushita, T.; Ebitani, K.; Kaneda, K. Chem. Commun. 1999, 265–266.
  • Friedrich, H. B.; Govender, M.; Makhoba, X.; Ngcobo, T. D.; Onani, M. O. The Os/Cu–Al-hydrotalcite Catalysed Hydroxylation of Alkenes. Chem. Commun. 2003, 23, 2922. DOI: https://doi.org/10.1039/B310686A.
  • Naicker, T.; Datye, A. K.; Friedrich, H. B. A Comparative Study of Os-hydrotalcites for the Cis-dihydroxylation of Cyclohexene. Applied Catal. A: Gen. 2008, 350(1), 96–102. DOI: https://doi.org/10.1016/j.apcata.2008.08.001.
  • Cavani, F.; Trifiro`, F.; Vaccari, A. Hydrotalcite-type Anionic Clays: Preparation, Properties and Applications. Catal. Today. 1991, 11(2), 173–301. DOI: https://doi.org/10.1016/0920-5861(91)80068-K.
  • Vaccari, A.;. Preparation and Catalytic Properties of Cationic and Anionic Clays. Catal. Today. 1998, 41(1–3), 53–71. DOI: https://doi.org/10.1016/S0920-5861(98)00038-8.
  • Qi, X.; Yoon, H.; Lee, S.-H.; Yoon, J.; Kim, S.-J. Surface-modified Imogolite by 3-APS–OsO4 Complex: Synthesis, Characterization and Its Application in the Dihydroxylation of Olefins. J. Ind Eng Chem. 2008, 14(1), 136–141. DOI: https://doi.org/10.1016/j.jiec.2007.08.010.
  • Lee, K.; Kim, Y.-H.; Han, S. B.; Kang, H.; Park, S.; Seok Seo, W.; Park, J. T.; Kim, B.; Chang, S. Osmium Replica of Mesoporous Silicate MCM-48: Efficient and Reusable Catalyst for Oxidative Cleavage and Dihydroxylation Reactions. J. Am. Chem. Soc. 2003, 23(125), 6844–6845. DOI: https://doi.org/10.1021/ja034137b.
  • Basavaraju, K. C.; Sharma, S.; Maurya, R. A.; Kim, D.-P. Cover Picture: Champagne and Fireworks: Angewandte Chemie Celebrates Its Birthday (Angew. Chem. Int. Ed. 1/2013). Angew. Chem. Int. Ed. 2013, 52(1), 1–5. DOI: https://doi.org/10.1002/anie.201209858.
  • (a) Choudary, B. M.; Jyothi, K.; Kantam, M. L.; Sreedhar, B. Achiral Dihydroxylation of Olefins by Osmate (Oso42−) Stabilised on Nanocrystalline Magnesium Oxide. Adv. Synth. Catal. 2004, 346(1), 45–48. DOI: https://doi.org/10.1002/adsc.200303133. (b) Choudary, B.M.; Chowdari, N. S.; Jyothi, K.; Kantam, M. L. J. Am. Chem. Soc. 2002, 124, 5341-5349.
  • (a) Jun, B.-H.; Kim, J.-H.; Park, J.; Kang, H.; Lee, S.-H.; Lee, Y.-S. Synlett. 2008, 2313–2316. (b) Jiang, R.; Kuang, Y.; Sun, X.; Zhang, S. Acta Chim. Slov. 2005, 52, 467-470; (c) Kim, K. J.; Choi, H.Y; Hwang, S.H.; Park, Y.S.; Kwueon, E.K.; Choi, D.S.; Song, C.E.; Chem. Commun. 2005, 3337-3339; (d) Ley, S.V.; Ramarao, C.; Lee, A.-L.; Østergaard, N.; Smith, S.C.; Shirley, I.M. Org. Lett. 2003, 5, 185-187; (e) Lee, B.S.; Mahajan, S.; Janda, K.D.; Tetrahedron Lett. 2005, 46, 4491-4493.
  • Kobayashi, S.; Endo, M.; Nagayama, S. Catalytic Asymmetric Dihydroxylation of Olefins Using a Recoverable and Reusable Polymer-Supported Osmium Catalyst. J. Am. Chem. Soc. 1999, 121(48), 11229–11230. DOI: https://doi.org/10.1021/ja993099m.
  • Kim, K. J.; Choi, H. Y.; Hwang, S. H.; Park, Y. S.; Kwueon, E. K.; Choi, D. S.; Song, C. E. Markedly Enhanced Recyclability of Osmium Catalyst in Asymmetric Dihydroxylation Reactions by Using Macroporous Resins Bearing Both Residual Vinyl Groups and Quaternary Ammonium Moieties. Chem. Commun. 2005, 26, 3337–3339. DOI: https://doi.org/10.1039/b504223b.
  • Leurs, M.; Spiekermann, P. S.; Tiller, J. C. Optimization of and Mechanistic Considerations for the Enantioselective Dihydroxylation of Styrene Catalyzed by Osmate-Laccase-Poly(2-Methyloxazoline) in Organic Solvents. ChemCatChem. 2016, 8(3), 593–599. DOI: https://doi.org/10.1002/cctc.201501083.
  • Leurs, M.; Dorn, B.; Wilhelm, S.; Manisegaran, M.; Tiller, J. C. Multicore Artificial Metalloenzymes Derived from Acylated Proteins as Catalysts for the Enantioselective Dihydroxylation and Epoxidation of Styrene Derivatives. Chem. Eur. J. 2018, 24(42), 10859–10867. DOI: https://doi.org/10.1002/chem.201802185.
  • Allard, M.; Dupont, C.; Robles, V. M.; Doucet, N.; Lledos, A.; Marechal, J. D.; Urvoas, A.; Mahy, J. P.; Ricoux, R. Incorporation of Manganese Complexes into Xylanase: New Artificial Metalloenzymes for Enantioselective Epoxidation. ChemBioChem. 2012, 13(2), 240. DOI: https://doi.org/10.1002/cbic.201100659.
  • Okrasa, K.; Kazlauskas, R. J. Manganese-Substituted Carbonic Anhydrase as a New Peroxidase. Chem. Eur. J. 2006, 12(6), 1587–1596. DOI: https://doi.org/10.1002/chem.200501413.
  • Fernandez-Gacio, A.; Codina, A.; Fastrez, J.; Riant, O.; Soumillion, P. Transforming Carbonic Anhydrase into Epoxide Synthase by Metal Exchange. ChemBioChem. 2006, 7(7), 1013–1016. DOI: https://doi.org/10.1002/cbic.200600127.
  • Sugimoto, H.; Kitayama, K.; Mori, S.; Itoh, S. An Osmium (Iii)/osmium (V) Redox Couple Generating OsV (O)(OH) Center for Cis-1, 2-Dihydroxylation of Alkenes with H2O2: Os Complex with a Nitrogen-Based Tetradentate Ligand. J. Am. Chem. Soc. 2012, 134(46), 19270. DOI: https://doi.org/10.1021/ja309566c.
  • Sugimoto, H.; Ashikari, K.; Itoh, S. Osmium(III) and Osmium(V) Complexes Bearing A Macrocyclic Ligand: A Simple and Efficient Catalytic System for cis-Dihydroxylation of Alkenes with Hydrogen Peroxide. Chem. Asian J. 2013, 8(9), 2154–2160. DOI: https://doi.org/10.1002/asia.201300329.
  • Kaur, A.; Singh, V. Synlett. 2014, 26, 1191–1194.
  • Chen, M.; Pan, Y.; Kwong, H.-W.; Zeng, R. J.; Lau, K.-C.; Lau, T.-C. Catalytic Oxidation of Alkanes by a (Salen)osmium(vi) Nitrido Complex Using H2O2 as the Terminal Oxidant. Chem. Commun. 2015, 51(71), 13686–13689. DOI: https://doi.org/10.1039/C5CC03636D.
  • Fujimoto, T.; Sugimoto, H.; Kai, K.; Maeda, K.; Itoh, S. Oxido-Hydroxido- and Oxido-Aminato-Osmium(V) Complexes with a Cyclohexanediamine-Based Tetradentate Ligand as Active Oxidants for Dihydroxylation and Aminohydroxylation of Alkenes. Eur. J. Inorg. Chem. 2019, 2019(24), 2891–2898. DOI: https://doi.org/10.1002/ejic.201900339.
  • Kelebekli, L.; Atlı, I. Stereoselective Synthesis of a New Methyl-substituted Inositol Derivative. Tetrahedron. 2019, 75(38), 130531. DOI: https://doi.org/10.1016/j.tet.2019.130531.

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