Academic literature on the topic 'Osmylation'

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Journal articles on the topic "Osmylation"

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Brovetto, Margarita, Valeria Schapiro, Gabriel Cavalli, Paula Padilla, Ana Sierra, Gustavo Seoane, Leopoldo Suescun, and Raul Mariezcurrena. "Osmylation of chiral cis-cyclohexadienediols." New Journal of Chemistry 23, no. 5 (1999): 549–55. http://dx.doi.org/10.1039/a900732f.

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Tsui, Hon-Chung, and Leo A. Paquette. "Olefin Cleavage under Osmylation Conditions." Journal of Organic Chemistry 63, no. 22 (October 1998): 8071–73. http://dx.doi.org/10.1021/jo9812983.

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Al-Fouti, Khaled, and James R. Hanson. "The Stereochemistry of Osmylation of 2- and 17-Methylene-5α-Androstanes." Journal of Chemical Research 2003, no. 4 (April 2003): 232–33. http://dx.doi.org/10.3184/030823403103173606.

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Osmylation of 2-methylene-5α-androstan-17-one has been shown to afford the 2α-hydroxy-2β-hydroxymethyl derivative whilst 3β-hydroxy-17-methylene-5α-androstane gives the 17α-hydroxy-17β-hydroxymethyl derivative; the facial selectivity of these reactions is discussed.
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BAUM, RUDY. "C enantiomers resolved by osmylation technique." Chemical & Engineering News 71, no. 26 (June 28, 1993): 35–36. http://dx.doi.org/10.1021/cen-v071n026.p035.

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Gurjar, M. K., and Anupama S Mainkar. "Catalytic osmylation of allyl D-glucopyranoside." Tetrahedron: Asymmetry 3, no. 1 (January 1992): 21–24. http://dx.doi.org/10.1016/s0957-4166(00)82306-x.

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Jarosz, Sławomir. "Osmylation of higher sugar allylic alcohols." Carbohydrate Research 183, no. 2 (December 1988): 209–15. http://dx.doi.org/10.1016/0008-6215(88)84075-8.

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Poli, Giovanni. "The osmylation of flexible 3-substituted cyclopentenes." Tetrahedron Letters 30, no. 52 (January 1989): 7385–88. http://dx.doi.org/10.1016/s0040-4039(00)70704-0.

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Annunziata, Rita, Mauro Cinquini, Franco Cozzi, and Laura Raimondi. "Stereoselective osmylation of 5-vinyl-4,5-dihydroisoxazoles." Journal of the Chemical Society, Chemical Communications, no. 7 (1985): 403. http://dx.doi.org/10.1039/c39850000403.

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Cui, Marko Burghard, and Klaus Kern. "Reversible Sidewall Osmylation of Individual Carbon Nanotubes." Nano Letters 3, no. 5 (May 2003): 613–15. http://dx.doi.org/10.1021/nl034135p.

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Français, Antoine, Olivier Bedel, and Arnaud Haudrechy. "Is osmylation always preferring the richest double bond?" Tetrahedron 64, no. 11 (March 2008): 2495–524. http://dx.doi.org/10.1016/j.tet.2007.11.068.

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Dissertations / Theses on the topic "Osmylation"

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Williams, Alvin Scott. "Charge transfer induced osmylation of aromatic compounds." Thesis, University College London (University of London), 1995. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.309472.

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Al-Fouti, Khaled. "Stereochemical and biotransformation studies in the steroid series." Thesis, University of Sussex, 2001. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.367770.

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Park, Christine Young-In. "Catalytic osmylation of dienes : mechanistic studies and applications to the stereoselective synthesis of polyols." Thesis, Massachusetts Institute of Technology, 1991. http://hdl.handle.net/1721.1/8834.

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Oliver, Patricia Ann. "The effects of allylic substituents on osmylation and epoxidation facial selectivities." 1993. http://catalog.hathitrust.org/api/volumes/oclc/31176943.html.

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Book chapters on the topic "Osmylation"

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Taber, Douglass F. "C–O Ring Construction: Sauropus Hexoside (Xie/Wu), (+)-Ipomeamarone (Usuki), Decytospolide A (Fujioka), Cytospolide P (Goswami), (+)-Didemniserinolipid B (Tong), Gymnothelignan N (She)." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0051.

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A range of biological activity was observed for the group of 3,6-anhydro-2-deoxy hexosides, of which 3 is representative, isolated from Sauropus rostratus. Wei-Jia Xie and Xiao-Ming Wu of China Pharmaceutical University prepared (Org. Lett. 2014, 16, 5004) 3 by the dealkylative cyclization of 1 to 2. (+)-Ipomeamarone 6 is a phytoalexin isolated from mold-damaged sweet pota­toes. Yoshinosuke Usuki of Osaka City University assembled (Chem. Lett. 2014, 43, 1882) 6 by the diastereoselective cyclization of 4 to 5. Hiromichi Fujioka of Osaka University protected (Org. Lett. 2014, 16, 3680) the enone of 7 by the conjugate addition of triphenylphosphine. Diastereoselective reduc­tion of the other ketone followed by deprotection of the enone and cyclization led to 8, that was hydrogenated to decytospolide A 9. En route to cytospolide P 12, Rajib Kumar Goswami of the Indian Association for the Cultivation of Science had planned (J. Org. Chem. 2014, 79, 7689) the ring-closing metathesis of 10. This failed, but cyclization of the corresponding silyl ether to 11 was successful with the second-generation Hoveyda catalyst. Rongbiao Tong of the Hong Kong University of Science and Technology set (J. Org. Chem. 2014, 79, 6987) the absolute configuration of (+)-didemniserinolipid B 15 by Sharpless asymmetric osmylation of the alkene 13. Oxidative Achmatowicz rearrangement/bicycloketalization then delivered 14. Xuegong She of Lanzhou University observed (Org. Lett. 2014, 16, 4440) remark­able diastereoselectivity in the reductive cyclization of 16 to 17. Oxidation of 17 led to regioselective cyclization to gymnothelignan N 18.
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Zhang, Hongmin, and Eli Ruckenstein. "A Novel Successive Route to Well-Defined Water-Soluble Poly(2,3-dihydroxypropyl methacrylate) and Amphiphilic Block Copolymers Based on an Osmylation Reaction *." In Solution and Surface Polymerization, 23–39. CRC Press, 2019. http://dx.doi.org/10.1201/9780429027420-3.

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Taber, Douglass F. "Arrays of Stereogenic Centers: The Davies Synthesis of Acosamine." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0041.

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Babak Borhan of Michigan State University found (Angew. Chem. Int. Ed. 2011, 50, 2593) that the ligand developed for asymmetric osmylation worked well for the enantioselective cyclization of 1 to 2. Kyungsoo Oh of IUPUI devised (Org. Lett. 2011, 13, 1306) a Co catalyst for the stereocontrolled addition of 4 to 3 to give 5. Michael J. Krische of the University of Texas Austin prepared (Angew. Chem. Int. Ed. 2011, 50, 3493) 8 by Ir*-mediated oxidation/addition of 7 to 6. Yixin Lu of the National University of Singapore employed (Angew. Chem. Int. Ed. 2011, 50, 1861) an organocatalyst to effect the stereocontrolled addition of 10 to 9. Naoya Kumagai and Masakatsu Shibasaki of the Institute of Microbial Chemistry, Tokyo took advantage (J. Am. Chem. Soc. 2011, 133, 5554) of the soft Lewis basicity of 13 to effect stereocontrolled condensation with 12. Yujiro Hayashi of the Tokyo University of Science found (Angew. Chem. Int. Ed. 2011, 50, 2804, not illustrated) that aqueous chloroacetaldehyde participated well in crossed aldol condensations. Andrew V. Malkov, now at Loughborough University, and Pavel Kocovsky of the University of Glasgow showed (J. Org. Chem. 2011, 76, 4800) that the inexpensive mixed crotyl silane 16 could be added to 15 with high stereocontrol. Shigeki Matsunaga of the University of Tokyo and Professor Shibasaki opened (J. Am. Chem. Soc. 2011, 133, 5791) the meso aziridine 18 with malonate 19 to give 20. Masahiro Terada of Tohoku University effected (Org. Lett. 2011, 13, 2026) the conjugate addition of 22 to 21 with high stereocontrol. Jinxing Ye of the East China University of Science and Technology reported (Angew. Chem. Int. Ed. 2011, 50, 3232, not illustrated) a related conjugate addition. Kian L. Tian of Boston College observed (Org. Lett. 2011, 13, 2686) that the kinetic hydroformylation of 24 set the relative configuration of two stereogenic centers. Alexandre Alexakis and Clément Mazet of the Université de Genève established (Angew. Chem. Int. Ed. 2011, 50, 2354) a tandem one-pot procedure for the addition of 26 to 27 to give 28.
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Taber, Douglass. "Stereocontrolled Construction of Arrays of Stereogenic Centers." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0041.

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Complex natural products and even some complex pharmaceuticals contain arrays of stereogenic centers. Sometimes, the desired array is readily available from a natural product, but usually, such arrays of multiple stereogenic centers must be assembled. Armando Córdova of Stockholm University has reported (Angew. Chem. Int. Ed. 2007, 46, 778) a simple procedure for the organocatalyst-mediated addition of the nitrene equivalent 2 to an α, β-unsaturated aldehyde to give the protected aziridine 4 in high ee. Organocatalysis was also used (Organic Lett. 2007, 9, 1001) by Arumugam Sudalai of the National Chemical Laboratory, Pune, to effect coupling of the aldehyde 5 with dibenzylazodicarboxylate 6 to give, following the List procedure, the intermediate aldehyde 7. Osmylation of the derived unsaturated ester 8 proceeded with high diastereocontrol, to give 9. Products 4 and 9 have adjacent stereogenic centers. Hisashi Yamamoto of the University of Chicago has introduced (J. Am. Chem. Soc. 2007, 129, 2762) the linchpin reagent acetaldehyde “super”silyl enol ether 11. Diastereoselective addition of 11 to the enantiomerically-pure aldehyde 10, with concomitant silyl transfer, followed by the addition of allyl magnesium bromide delivered the protected triol 12 in high de and ee. Arrays that combine alkylated and oxygenated or aminated centers are also important. Akio Kamimura of Yamaguchi University took (J. Org. Chem. 2007, 72, 3569) a Baylis- Hillman like approach, adding thiophenoxide to t -butyl acrylate in the presence of an enantiomerically-pure aldehyde N-sulfinimine such as 13 to give the adduct 14 with high diastereocontrol. Keiji Maruoka of Kyoto University has designed (Angew. Chem. Int. Ed. 2007, 46, 1738) the chiral amine 17, that catalyzed the condensation of an aldehyde with ethyl glyoxylate 16 with high enantiocontrol. In a very thoughtful approach, Liu-Zhu Gong of the University of Science and Technology of China in Hefei extended (Chem. Commun. 2007, 736) the now-classic aldol condensation of cyclohexanone to 4-substituted cyclohexanones such as 19. The product 21 could be carried in many directions, including to the Bayer-Villiger product 22. Arrays of alkylated and polyalkylated centers have been among the most challenging to prepare.
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Taber, Douglass F. "Enantioselective Synthesis of Alcohols and Amines: The Doi Synthesis of Apratoxin C." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0034.

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Hiromitsu Takayama of Chiba University used (Org. Lett. 2014, 16, 5000) the Itsuno-Corey protocol to reduce the enone 1 to the allylic alcohol 2. Peiming Gu of Ningxia University developed (Org. Lett. 2014, 16, 5339) a Cu catalyst that cyclized the pro­chiral 3 to 4 in high ee. Xiaoming Feng of Sichuan University effected (Org. Lett. 2014, 16, 3938) enantioselective Baeyer–Villiger oxidation of the racemic cyclopentanone 5, converting one enantiomer to the δ-lactone 6. The velocity of catalytic osmylation is often limited by slow turnover of the interme­diate osmate ester. Koichi Narasaka, then at the University of Tokyo, showed (Chem. Lett. 1988, 1721) that the efficiency of the transformation was improved by the addi­tion of stoichiometric phenyl boronic acid. Kilian Muñiz, now at ICIQ Tarragona, established (Chem. Eur. J. 2005, 11, 3951) that this acceleration also worked with Sharpless asymmetric dihydroxylation. D. Christopher Braddock of Imperial College London took advantage (Chem. Commun. 2014, 50, 13725) of these observations, converting myrcene 7 selectively to the cyclic boronate 8. Michael P. Doyle of the University of Maryland developed (J. Org. Chem. 2014, 79, 12185) a Rh catalyst for the ene reaction of 9 with 10 to give 11. Adriaan J. Minnaard of the University of Groningen devised (Chem. Eur. J. 2014, 20, 14250) a Cu cata­lyst that mediated the face selective addition of 13 to 12, establishing the oxygenated quaternary center of 14. Tomonori Misaki and Takashi Sugimura of the University of Hyogo used (Chem. Lett. 2014, 43, 1826) Michael addition of 15 to 16 to construct the oxygenated quaternary center of 17. Jon C. Antilla of the University of South Florida assembled (Chem. Commun. 2014, 50, 14187) the δ-lactone 20 by adding the diene 19 to the α-keto ester 18. Zhiyong Wang of the University of Science and Technology of China reported (Org. Lett. 2014, 16, 3564) related results. Jonathan A. Ellman of Yale University achieved (Angew. Chem. Int. Ed. 2014, 53, 11329) substantial enantioselectivity in the addition of thioacetic acid 22 to the nitroalkene 21 to give 23. Subhash P. Chavan of the National Chemistry Laboratory prepared (Tetrahedron Lett. 2014, 55, 5905) the allylic amine 25 by reduction of the aziridine 24.
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