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The structure of osmium tetraoxide-cinchona alkaloid complexes

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    The structure of osmium tetraoxide-cinchona alkaloid complexes
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 1989, 54, 10, 2263–2264
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    https://doi.org/10.1021/jo00271a002
    Published May 1, 1989
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    1. Sergi Burguera, Antonio Frontera. Osme Bonds in Molecular Crystals: Structural Insights, Substituent Effects, and Energetic Features. Crystal Growth & Design 2025, 25 (11) , 3949-3957. https://doi.org/10.1021/acs.cgd.5c00371
    2. G. K. Surya Prakash, Fang Wang, Martin Rahm, Zhe Zhang, Chuanfa Ni, Jingguo Shen, and George A. Olah . The Trifluoromethyl Group as a Conformational Stabilizer and Probe: Conformational Analysis of Cinchona Alkaloid Scaffolds. Journal of the American Chemical Society 2014, 136 (29) , 10418-10431. https://doi.org/10.1021/ja504376u
    3. Kilian Muñiz and, Martin Nieger. Ferrocenoyl-Substituted Cinchona Alkaloids:  Synthesis, Structure, and Application in Asymmetric Catalytic Oxidation. Organometallics 2003, 22 (22) , 4616-4619. https://doi.org/10.1021/om0304457
    4. James P. Collman,, LeGrande M. Slaughter,, Todd A. Eberspacher,, Thomas Strassner, and, John I. Brauman. Mechanism of Dihydrogen Cleavage by High-Valent Metal Oxo Compounds:  Experimental and Computational Studies. Inorganic Chemistry 2001, 40 (24) , 6272-6280. https://doi.org/10.1021/ic010639j
    5. Michael Gerken,, David A. Dixon, and, Gary J. Schrobilgen. The OsO4F-, OsO4F22-, and OsO3F3- Anions, Their Study by Vibrational and NMR Spectroscopy and Density Functional Theory Calculations, and the X-ray Crystal Structures of [N(CH3)4][OsO4F] and [N(CH3)4][OsO3F3]. Inorganic Chemistry 2000, 39 (19) , 4244-4255. https://doi.org/10.1021/ic000259i
    6. Per-Ola Norrby,, Torben Rasmussen,, Jan Haller,, Thomas Strassner, and, K. N. Houk. Rationalizing the Stereoselectivity of Osmium Tetroxide Asymmetric Dihydroxylations with Transition State Modeling Using Quantum Mechanics-Guided Molecular Mechanics. Journal of the American Chemical Society 1999, 121 (43) , 10186-10192. https://doi.org/10.1021/ja992023n
    7. Derek W. Nelson,, Andreas Gypser,, Pui Tong Ho,, Hartmuth C. Kolb,, Teruyuki Kondo,, Hoi-Lun Kwong,, Dominic V. McGrath,, A. Erik Rubin,, Per-Ola Norrby,, Kevin P. Gable, and, K. Barry Sharpless. Toward an Understanding of the High Enantioselectivity in the Osmium-Catalyzed Asymmetric Dihydroxylation. 4. Electronic Effects in Amine-Accelerated Osmylations. Journal of the American Chemical Society 1997, 119 (8) , 1840-1858. https://doi.org/10.1021/ja961464t
    8. Andrea Daolio, Andrea Pizzi, Miriam Calabrese, Giancarlo Terraneo, Simone Bordignon, Antonio Frontera, Giuseppe Resnati. Molecular Electrostatic Potential and Noncovalent Interactions in Derivatives of Group 8 Elements. Angewandte Chemie 2021, 133 (38) , 20891-20895. https://doi.org/10.1002/ange.202107978
    9. Andrea Daolio, Andrea Pizzi, Miriam Calabrese, Giancarlo Terraneo, Simone Bordignon, Antonio Frontera, Giuseppe Resnati. Molecular Electrostatic Potential and Noncovalent Interactions in Derivatives of Group 8 Elements. Angewandte Chemie International Edition 2021, 60 (38) , 20723-20727. https://doi.org/10.1002/anie.202107978
    10. David J. Ager. Cinchona Alkaloids as Chiral Ligands in Asymmetric Oxidations. 2009, 29-71. https://doi.org/10.1002/9783527628179.ch3
    11. Mariappan Periasamy, Sakilam Satish Kumar, N. Sampath Kumar. Catalytic asymmetric dihydroxylation of substituted trans-stilbene derivatives: implications of the variation of enantioselectivities on the mechanism of OsO4 addition to olefins. Tetrahedron Letters 2008, 49 (28) , 4416-4419. https://doi.org/10.1016/j.tetlet.2008.05.016
    12. Jennifer A. Bodkin, George B. Bacskay, Malcolm D. McLeod. The Sharpless asymmetric aminohydroxylation reaction: optimising ligand/substrate control of regioselectivity for the synthesis of 3- and 4-aminosugars. Organic & Biomolecular Chemistry 2008, 6 (14) , 2544. https://doi.org/10.1039/b803310b
    13. Mark C. Noe, Michael A. Letavic, Sheri L. Snow, . Asymmetric Dihydroxylation of Alkenes. 2005, 109-625. https://doi.org/10.1002/0471264180.or066.02
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    20. Roland Hubel, Kurt Polborn, Wolfgang Beck. Cinchona Alkaloids as Versatile Ambivalent Ligands – Coordination of Transition Metals to the Four Potential Donor Sites of Quinine. European Journal of Inorganic Chemistry 1999, 1999 (3) , 471-482. https://doi.org/10.1002/(SICI)1099-0682(199903)1999:3<471::AID-EJIC471>3.0.CO;2-H
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    24. Ulrich Pidun, Christian Boehme, Gernot Frenking. Theoretische Untersuchungen schließen eine [2 + 2]‐Addition als einleitenden Schritt der Osmiumtetroxid‐katalysierten Dihydroxylierung von Alkenen aus. Angewandte Chemie 1996, 108 (23-24) , 3008-3011. https://doi.org/10.1002/ange.19961082330
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    27. Gregori Ujaque, Febu Maseras, Agustí Lledós. A theoretical evaluation of steric and electronic effects on the structure of [OSO4 (NR3)] (NR3 = bulky chiral alkaloid derivative) complexes. Theoretica Chimica Acta 1996, 94 (2) , 67-73. https://doi.org/10.1007/BF00194932
    28. Christina Moberg, Hans Adolfsson, Kenneth Wärnmark, Per‐Ola Norrby, Karl‐Magnus Marstokk, Harald Møllendal. Conformational Preference of 2‐(Halomethyl)‐ and 2‐(Oxymethyl)Pyridines: Microwave Spectrum, Ab Initio, and MM3 Studies of 2‐(Fluoromethyl)Pyridine. Chemistry – A European Journal 1996, 2 (5) , 516-522. https://doi.org/10.1002/chem.19960020510
    29. Christopher Missling, Shahram Mihan, Kurt Polborn, Wolfgang Beck. Metal Complexes of Biologically Important Ligands, LXXXVI. Organometallic Complexes of Ruthenium(II), Rhodium(III), Iridium(III), and Gold(I) with Cinchona Alkaloids. Chemische Berichte 1996, 129 (3) , 331-335. https://doi.org/10.1002/cber.19961290314
    30. Gernot Frenking, Iris Antes, Marlis Böhme, Stefan Dapprich, Andreas W. Ehlers, Volker Jonas, Arndt Neuhaus, Michael Otto, Ralf Stegmann, Achim Veldkamp, Sergei F. Vyboishchikov. Pseudopotential Calculations of Transition Metal Compounds: Scope and Limitations. 1996, 63-144. https://doi.org/10.1002/9780470125854.ch2
    31. Herbert Waldmann. Enantioselective cis ‐Dihydroxylation. 1995, 9-18. https://doi.org/10.1002/9783527619948.ch2
    32. Gilbert G. A. Balavoine, Eric Manoury. Organometallic compounds in asymmetric synthesis: Oxygen atom transfer. Applied Organometallic Chemistry 1995, 9 (3) , 199-225. https://doi.org/10.1002/aoc.590090305
    33. Per‐Ola Norrby, Kenneth Wärnmark, Björn Åkermark, Christina Moberg. Unusual conformational‐determining interactions in oxymethylpyridines: An ab initio study and an improved method for refining molecular mechanics parameters. Journal of Computational Chemistry 1995, 16 (5) , 620-627. https://doi.org/10.1002/jcc.540160510
    34. Sigeru Torii, Ping Liu, Hideo Tanaka. Electrochemical Os-Catalyzed Asymmetric Dihydroxylation of Olefins with Sharpless’ Ligand. Chemistry Letters 1995, 24 (4) , 319-320. https://doi.org/10.1246/cl.1995.319
    35. Joseph B. Sweeney. Alkyl Chalcogenides: Oxygen-based Functional Groups. 1995, 37-112. https://doi.org/10.1016/B0-08-044705-8/00250-8
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    Cite this: J. Org. Chem. 1989, 54, 10, 2263–2264
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jo00271a002
    Published May 1, 1989
    Request reuse permissions

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