CrossRef enabled

PAC Archives

Archive →

Pure Appl. Chem., 1983, Vol. 55, No. 11, pp. 1823-1836

http://dx.doi.org/10.1351/pac198355111823

On the mechanism of titanium-tartrate catalyzed asymmetric epoxidation

K. B. Sharpless and S. S. Woodard

CrossRef Cited-by theme picture

CrossRef Cited-by Linking

  • Reddy Jala R. C., Rao Bhamidipati V. S. K., Karuna Marellapudi S., Raju Kothapalli V. S. N., Krishna Achanta V. R., Prasad Rachapudi B. N.: Lipase-mediated preparation of epoxy lecithin and its evaluation as plasticizer in polyester laminates. J. Appl. Polym. Sci. 2013, 127, 2945. <http://dx.doi.org/10.1002/app.37960>
  • Shekhar Vanam, Reddy Dorigondla Kumar, Venkateswarlu Yenamandra: Total Synthesis of Umuravumbolide. HCA 2012, 95, 1593. <http://dx.doi.org/10.1002/hlca.201200078>
  • Newhouse Timothy R., Li Xin, Blewett Megan M., Whitehead Clare M. C., Corey E. J.: A Tetradentate Ligand for the Enantioselective Ti(IV)-Promoted Oxidation of Sulfides to Sulfoxides: Origin of Enantioselectivity. J. Am. Chem. Soc. 2012, 134, 17354. <http://dx.doi.org/10.1021/ja305991k>
  • Mungroo Rubeena, Goud Vaibhav V., Pradhan Narayan C., Dalai Ajay K.: Modification of epoxidised canola oil. Asia-Pacific Jrnl of Chem Eng 2011, 6, 14. <http://dx.doi.org/10.1002/apj.448>
  • Wu Jie, Panek James S.: Total Synthesis of (−)-Virginiamycin M2: Application of Crotylsilanes Accessed by Enantioselective Rh(II) or Cu(I) Promoted Carbenoid Si–H Insertion. J Org Chern 2011, 76, 9900. <http://dx.doi.org/10.1021/jo202119p>
  • Wu Jie, Panek James S.: Total Synthesis of (−)-Virginiamycin M2. Angew Chem 2010, 122, 6301. <http://dx.doi.org/10.1002/ange.201002220>
  • Wu Jie, Panek James S.: Total Synthesis of (−)-Virginiamycin M2. Angew Chem Int Ed 2010, 49, 6165. <http://dx.doi.org/10.1002/anie.201002220>
  • Cai Chuanshang, Dai Honghai, Chen Rongsheng, Su Caixia, Xu Xiaoya, Zhang Shi, Yang Liting: Studies on the kinetics ofin situ epoxidation of vegetable oils. Eur J Lipid Sci Technol 2008, 110, 341. <http://dx.doi.org/10.1002/ejlt.200700104>
  • Mungroo Rubeena, Pradhan Narayan C., Goud Vaibhav V., Dalai Ajay K.: Epoxidation of Canola Oil with Hydrogen Peroxide Catalyzed by Acidic Ion Exchange Resin. J Amer Oil Chem Soc 2008, 85, 887. <http://dx.doi.org/10.1007/s11746-008-1277-z>
  • Varela Michael C., Dixon Seth M., Lam Kit S., Schore Neil E.: Asymmetric epoxidation, Michael addition, and triple cascade reaction using polymer-supported prolinol-based auxiliaries. Tetrahedron 2008, 64, 10087. <http://dx.doi.org/10.1016/j.tet.2008.08.013>
  • Yadav J.S., Premalatha K., Harshavardhan S.J., Subba Reddy B.V.: The first stereoselective and the total synthesis of Leiocarpin C and total synthesis of (+)-Goniodiol. Tetrahetron Lett 2008, 49, 6765. <http://dx.doi.org/10.1016/j.tetlet.2008.08.078>
  • Aciro Caroline, Claridge Timothy D. W., Davies Stephen G., Roberts Paul M., Russell Angela J., Thomson James E.: Ammonium-directed dihydroxylation of 3-aminocyclohex-1-enes: development of a metal-free dihydroxylation protocol. Org Biomol Chem 2008, 6, 3751. <http://dx.doi.org/10.1039/b808811j>
  • Erker Gerhard: Group 4 metallocenes in bioorganometallic chemistry. J Organomet Chem 2007, 692, 1187. <http://dx.doi.org/10.1016/j.jorganchem.2006.11.023>
  • Sabitha Gowravaram, Reddy E. Venkata, Bhikshapathi M., Yadav J.S.: Total synthesis of (9S,12R,13S)-pinellic acid. Tetrahetron Lett 2007, 48, 313. <http://dx.doi.org/10.1016/j.tetlet.2006.11.004>
  • Tse Man Kin, Bhor Santosh, Klawonn Markus, Anilkumar Gopinathan, Jiao Haijun, Spannenberg Anke, Döbler Christian, Mägerlein Wolfgang, Hugl Herbert, Beller Matthias: Ruthenium-Catalyzed Asymmetric Epoxidation of Olefins Using H2O2, Part II: Catalytic Activities and Mechanism. Chem Eur J 2006, 12, 1875. <http://dx.doi.org/10.1002/chem.200501262>
  • Goud Vaibhav V., Pradhan Narayan C., Patwardhan Anand V.: Epoxidation of karanja (Pongamia glabra) oil by H2O2. J Amer Oil Chem Soc 2006, 83, 635. <http://dx.doi.org/10.1007/s11746-006-1250-7>
  • Mikami Koichi, Matsumoto Yousuke, Xu Ling: Modification of alkoxo ligands of BINOL–Ti ladder: Isolation and X-ray crystallographic analysis. Inorg Chim Ada 2006, 359, 4159. <http://dx.doi.org/10.1016/j.ica.2005.11.052>
  • Meyer zu Berstenhorst Birgit, Erker Gerhard, Kehr Gerald, Fr?hlich Roland: Carbohydrate?metallocene conjugates: selective formation of a zirconadioxacyclopentane-type dimer from the reaction of a bis(enolate)ZrCp2 reagent with a glucofuranoside derivative. Dalton Trans 2006, 3200. <http://dx.doi.org/10.1039/b603803d>
  • Yadav Jhillu Singh, Raju Atcha Krishnam, Rao Ponugoti Purushothama, Rajaiah Gurram: Highly stereoselective synthesis of antitumor agents: both enantiomers of goniothales diol, altholactone, and isoaltholactone. Tet Asymm 2005, 16, 3283. <http://dx.doi.org/10.1016/j.tetasy.2005.08.047>
  • Davies Stephen G., Long Marcus J. C., Smith Andrew D.: Ammonium directed dihydroxylation of N,N-dibenzylaminocyclohex-2-ene: metal-free syntheses of the diastereoisomers of 3-dibenzylamino-1,2-dihydroxycyclohexane. Chem Commun 2005, 4536. <http://dx.doi.org/10.1039/b509088a>
  • Snell Alexander, Kehr Gerald, Kataeva Olga, Fröhlich Roland, Erker Gerhard: Preparation and characterization of some structural variants of Cp*Ti(1,2-propandiolato) complexes. J Organomet Chem 2003, 687, 171. <http://dx.doi.org/10.1016/j.jorganchem.2003.06.002>
  • Yadav J.S, Geetha V, Krishnam Raju A, Gnaneshwar D, Chandrasekhar S: The first total synthesis of the 6-hydroxy-4E-sphingenines. Tetrahetron Lett 2003, 44, 2983. <http://dx.doi.org/10.1016/S0040-4039(03)00390-3>
  • Yadav J.S., Rajaiah G., Raju A.Krishnam: A concise and stereoselective synthesis of both enantiomers of altholactone and isoaltholactone. Tetrahetron Lett 2003, 44, 5831. <http://dx.doi.org/10.1016/S0040-4039(03)01413-8>
  • Mikami Koichi, Ohba Shiho, Ohmura Hirofumi: Regioselective, stereospecific, and chemoselective fluorination of epoxy alcohols: development of fluorinating hybrid reagents, associated with Lewis acid metal fluoride/ammonium hydrogen fluoride. J Organomet Chem 2002, 662, 77. <http://dx.doi.org/10.1016/S0022-328X(02)01888-0>
  • Yadav J.S, Kumar Mishra Rajesh: First total synthesis of strongylodiol A. Tetrahetron Lett 2002, 43, 1739. <http://dx.doi.org/10.1016/S0040-4039(02)00066-7>
  • Martinez Victor, Blais Jean-Claude, Astruc Didier: General Route from Simple Methyl, Alkyl, and Cycloalkyl Arenes to Polycyclic Cyclopentenyl Aryl Derivatives. The CpFe+ Group as an Activator and Tag. Org Lett 2002, 4, 651. <http://dx.doi.org/10.1021/ol0172875>
  • Yin Huiyong, Hachey David L., Porter Ned A.: Structural analysis of diacyl peroxides by electrospray tandem mass spectrometry with ammonium acetate: bond homolysis of peroxide-ammonium and peroxide-proton adducts. Rapid Commun Mass Spectrom 2000, 14, 1248. <http://dx.doi.org/10.1002/1097-0231(20000730)14:14<1248::AID-RCM18>3.0.CO;2-B>
  • Suresh P. S., Srinivasan M., Pillai V. N. Rajasekharan: Copolymers of polystyrene—New polymer supports for asymmetric epoxidation of allylic alcohols. J Polym Sci A Polym Chem 2000, 38, 161. <http://dx.doi.org/10.1002/(SICI)1099-0518(20000101)38:1<161::AID-POLA21>3.0.CO;2-2>
  • Brown John M., Leppard Simon J., Oakes John, Thornthwaite David: Diastereoselectivity in scalemic tartrate/titanium epoxidations. Chirality 2000, 12, 496. <http://dx.doi.org/10.1002/(SICI)1520-636X(2000)12:5/6<496::AID-CHIR35>3.0.CO;2-Y>
  • Schmittel Michael, Söllner Rolf: Electroactive Protecting Groups and Reaction Units, 6. – Titanium Enolate Radical Cations in Solution: Generation, Characterization, and Their Reactions. Chem Ber 1997, 130, 771. <http://dx.doi.org/10.1002/cber.19971300616>
  • Lattanzi Alessandra, Bonadies Francesco, Scettri Arrigo: Reactivity of furylhydroperoxides in asymmetric oxidation and kinetic resolution. Tet Asymm 1997, 8, 2141. <http://dx.doi.org/10.1016/S0957-4166(97)00202-4>
  • Talsi E.P., Shalyaev K.V.: 1H and 17O NMR spectroscopic detection and characterization of titanium (IV) alkylperoxo complex. Journal of Molecular Catalysis A 1996, 105, 131. <http://dx.doi.org/10.1016/1381-1169(95)00243-X>
  • Balavoine Gilbert G. A., Manoury Eric: Organometallic compounds in asymmetric synthesis: Oxygen atom transfer. Appl Organometal Chem 1995, 9, 199. <http://dx.doi.org/10.1002/aoc.590090305>
  • Eilerts Nancy W., Heppert Joseph A.: Bisphenol ligands in the stereocontrol of transformations catalyzed by titanium and tungsten. J Polyhedron 1995, 14, 3255. <http://dx.doi.org/10.1016/0277-5387(95)85010-4>
  • Pastó Mireia, Moyano Albert, Pericàs Miquel A., Riera Antoni: Enantioselective synthesis of fully protected anti 3-amino-2-hydroxy butyrates. Tet Asymm 1995, 6, 2329. <http://dx.doi.org/10.1016/0957-4166(95)00309-D>
  • Toba Makoto, Mizukami Fujio, Niwa Shu-ichi, Sanoa Tsuneji, Maedaa Kazuyuki, Annila Arto, Komppa Veikko, Moloy Kenneth G: Effect of the type of preparation on the properties of titania/silicas. Journal of Molecular Catalysis 1994, 91, 277. <http://dx.doi.org/10.1016/0304-5102(94)00040-9>
  • Markó István E, Evans Graham R, Declercq Jean-Paul: Catalytic asymmetric Diels-Alder reactions of 2-pyrone derivatives. Tetrahedron 1994, 50, 4557. <http://dx.doi.org/10.1016/S0040-4020(01)89387-X>
  • Kotha Sambasivarao: Opportunities in asymmetric synthesis: An industrial prospect. Tetrahedron 1994, 50, 3639. <http://dx.doi.org/10.1016/S0040-4020(01)90388-6>
  • Barton Derek H.R., Gateau-Olesker Alice, Géro Stephan D., Lacher Brigitte, Tachdjian Catherine, Zard Samir Z.: Radical decarboxylative alkylation of tartaric acid. Tetrahedron 1993, 49, 4589. <http://dx.doi.org/10.1016/S0040-4020(01)81288-6>
  • Antonioletti Roberto, Arista Luca, Bonadies Francesco, Locati Ludovica, Scettri Arrigo: Acid-catalyzed oxidation of furan derivatives by t-butyl hydroperoxide. Tetrahetron Lett 1993, 34, 7089. <http://dx.doi.org/10.1016/S0040-4039(00)61606-4>
  • Ferraboschi Patrizia, Casati Silvana, Grisenti Paride, Santaniello Enzo: A chemoenzymatic approach to enantiomerically pure (R)- and (S)-2,3-epoxy-2-(4-pentenyl)-propanol, a chiral building block for the synthesis of (R)- and (S)-frontalin. Tet Asymm 1993, 4, 9. <http://dx.doi.org/10.1016/S0957-4166(00)86004-8>
  • Peschke Bernd, Lüßmann Jörg, Hoppe Dieter, Dyrbusch Zzmichael: Diastereo- and enantioselective synthesis of 1,2:5,6-diepoxy-4-hydroxyalkyl carbamates. – regioselective ring opening and their transformation into doublyC-branched deoxy sugar analogues. Chem Ber 1992, 125, 1421. <http://dx.doi.org/10.1002/cber.19921250620>
  • Raifeld Yuri E., Vid Galina Ya., Mikerin Igor E., Arshava Boris M., Nikitenko Antonia A.: Total stereo- and enantio-selective synthesis of 2,3-dideoxy-3-C-methylene-d-glycero-pentose and its ethyl furanosides. Carbohydrates Research 1992, 224, 103. <http://dx.doi.org/10.1016/0008-6215(92)84097-C>
  • Erker Gerhard, Rump Mathias, Krüger Carl, Nolte Matthias: Structures and dynamic features of dinuclear tartratozirconocene complexes. Inorg Chim Ada 1992, 198-200, 679. <http://dx.doi.org/10.1016/S0020-1693(00)92413-7>
  • Erker Gerhard, Dehnicke Stefan, Rump Mathias, Krüger Carl, Werner Stefan, Nolte Matthias: Konkurrierendes Auftreten von isomeren (Dialkyltartrato)zirconocen-Dimeren mit Dimetallatricyclus- und zehngliedrigen Dimetallamonocyclus-Gerüsten. Angew Chem 1991, 103, 1371. <http://dx.doi.org/10.1002/ange.19911031028>
  • Marson Charles M., Benzies David W.M., Hobson Adrian D.: Stereocontrolled syntheses of hydroxylated tricyclic systems by a new annulation of 2-cyclohexen-1-one. Tetrahedron 1991, 47, 5491. <http://dx.doi.org/10.1016/S0040-4020(01)80982-0>
  • S Yadav J, Radhakrishna P: Synthesis of (9z,15z)-(11s,12s,13s)-11-hydroxy-12,13-epoxyoctadecadienoic acid : Application of 'sharpless kinetic resolution' to allyl propargyl alcohols. Tetrahedron 1990, 46, 5825. <http://dx.doi.org/10.1016/S0040-4020(01)87778-4>
  • Gill Melvyn, Smrdel Albin F.: Pigments of fungi, part 16. Synthesis of methyl (R)-(+)-tetrahydro-2-methyl-5-oxo-2-furanacetate and its (S)-(−)-antipode, chiroptical references for determination of the absolute stereochemistry of fungal pre-anthraquinones. Tet Asymm 1990, 1, 453. <http://dx.doi.org/10.1016/S0957-4166(00)86350-8>
  • Choudary B. M., Rani S. Shobha, Kantam M. Lakshmi: Selective Nucleophilic Openings Of 2,3-Epoxy Alcohols Catalysed By Pd(Pph3)4. Synth Common 1990, 20, 2313. <http://dx.doi.org/10.1080/00397919008053174>
  • Lou Bo-Liang, Zhang Ying-Zhi, Guo Guang-Zong, Dai Li-Xin: Regioselective halide attack on 2,3-epoxyalcohols by complex metal halides. Acta Chim Sin 1989, 7, 554. <http://dx.doi.org/10.1002/cjoc.19890070612>
  • Albinati A., Arz C., Pregosin P.S.: Asymmetric synthesis of complexed cyclic N,O-Acetals by use of platinum(II) complexes. Crystal structure of trans-[PtCl2(C2H4)(2-p-NO2C6H4)]. J Organomet Chem 1989, 371, C18. <http://dx.doi.org/10.1016/0022-328X(89)85219-2>
  • Coxon James M., van Eyk Stephen J., Steel Peter J.: Diastereoselectivity, diastereofacial selectivity and regioselectivity in the reactions of cannamyl chloride with aldehydes mediated by tin and aluminium. Tetrahedron 1989, 45, 1029. <http://dx.doi.org/10.1016/0040-4020(89)80014-6>
  • Krief A., Dumont W., Pasau P., Lecomte Ph.: Stereoselective synthesis of methyl (1R) - and (1R) -hemicaronaldehydes from natural tartaric acid: Application to the synthesis of s-bioallethrin and deltamethrin insecticides§. Tetrahedron 1989, 45, 3039. <http://dx.doi.org/10.1016/S0040-4020(01)80130-7>
  • Ojima Iwao, Clos Núria, Bastos Cecilia: Recent advances in catalytic asymmetric reactions promoted by transition metal complexes. Tetrahedron 1989, 45, 6901. <http://dx.doi.org/10.1016/S0040-4020(01)89159-6>
  • Conte Valeria, Di Furia Fulvio, Licini Giulia, Modena Giorgio: Asymmetric oxidation of thioethers. Tetrahetron Lett 1989, 30, 4859. <http://dx.doi.org/10.1016/S0040-4039(01)80528-1>
  • Crombie Leslie, Jarrett Sandra R.M.: Synthesis of the host-selective plant toxins AF IIa, AF IIc and AKII, employing sharpless chiral epoxidation under kinetic control. Tetrahetron Lett 1989, 30, 4303. <http://dx.doi.org/10.1016/S0040-4039(01)80716-4>
  • Schmidt Richard R., Frische Klaus: De-novo-Synthese von Kohlenhydraten und verwandten Naturstoffen, 29. Synthese von partiell geschützten Zuckern ausmeso-Divinylglycol. Liebigs Ann Chem 1988, 1988, 209. <http://dx.doi.org/10.1002/jlac.198819880305>
  • Jarosz Sławomir: Stereoselective reduction of higher sugar enones with zinc borohydride. Carbohydrates Research 1988, 183, 201. <http://dx.doi.org/10.1016/0008-6215(88)84074-6>
  • Jarosz Sławomir: Epoxidation of higher sugar allylic alcohols. Carbohydrates Research 1988, 183, 217. <http://dx.doi.org/10.1016/0008-6215(88)84076-X>
  • Aziz Mostafa, Rouessac Francis: Syntheses en serie racemique et en serie optiquement active d'une famille de derives oxygenes naturels de l'ombelliferone. Structure spatiale du (-)epoxy-3'6' auraptene. Tetrahedron 1988, 44, 101. <http://dx.doi.org/10.1016/S0040-4020(01)85097-3>
  • Feringa Ben L., De Lange Ben: Asymmetric 1,4-additions to 5-alkoxy-2(5h)-furanones. Tetrahedron 1988, 44, 7213. <http://dx.doi.org/10.1016/S0040-4020(01)86092-0>
  • Wagler Thomas R., Burrows Cynthia J.: Synthesis of a chiral dioxo-cyclam derived from L-phenylalanine and its application to olefin oxidation chemistry. Tetrahetron Lett 1988, 29, 5091. <http://dx.doi.org/10.1016/S0040-4039(00)80687-5>
  • Rao A. V. Rama, Khrimian A. P., Krishna P. Radha, Yadagiri P., Yadav J. S.: Study on Sharpless Kinetic Resol Ution of Racemic Allyl Propargyl Alcohols. Synth Common 1988, 18, 2325. <http://dx.doi.org/10.1080/00397918808082377>
  • Thiem Joachim, Schöttmer Bernhard: β-Glycosylierung bei 2-Desoxysacchariden: Konvergente Synthesen der Oligosaccharide von Mithramycin. Angew Chem 1987, 99, 591. <http://dx.doi.org/10.1002/ange.19870990626>
  • Küfner Ulrike, Schmidt Richard R.: Synthesis of 4,6-diedoxy-d- and -l-hexoses from racemic and meso-dipropenylglycol. Carbohydrates Research 1987, 161, 211. <http://dx.doi.org/10.1016/S0008-6215(00)90078-8>
  • Boivin Taryn L.B.: Synthetic routes to tetrahydrofuran, tetrahydropyran, and spiroketal units of polyether antibiotics and a survey of spiroketals of other natural products. Tetrahedron 1987, 43, 3309. <http://dx.doi.org/10.1016/S0040-4020(01)81626-4>
  • Aziz Mostafa, Rouessac Francis: Syntheses de la (+)-marmine, des (+)-epoxy-6′,7′- et (-)-epoxy-3′,6′-auraptenes et des racemiques correspondants. Tetrahetron Lett 1987, 28, 2579. <http://dx.doi.org/10.1016/S0040-4039(00)96152-5>
  • Küfner Ulrike, Schmidt Richard R.: De-novo-Synthese von Kohlenhydraten und verwandten Naturstoffen, 22. Synthese derD-Digitoxose ausmeso-Divinylglycol. Liebigs Ann Chem 1986, 1986, 1600. <http://dx.doi.org/10.1002/jlac.198619860909>
  • Markó László: Transition metals in organic synthesis: Hydroformylation, reduction and oxidation. J Organomet Chem 1986, 305, 333. <http://dx.doi.org/10.1016/0022-328X(86)80167-X>
  • Hegedus Louis S.: Transition metals in organic synthesis annual survey covering the year 1984. J Organomet Chem 1986, 298, 207. <http://dx.doi.org/10.1016/0022-328X(86)82006-X>
  • Takata Toshikazu, Ando Wataru: Asymmetric oxidation of racemic sulfide. Stereochemistry of enantiomer differentiation reaction. Tetrahetron Lett 1986, 27, 1591. <http://dx.doi.org/10.1016/S0040-4039(00)84322-1>
  • Miyashita Akira, Ishida Jun-ya, Nohira Hiroyuki: Novel oxirane formation via 1-metalla-2-oxacyclobutanes. Tetrahetron Lett 1986, 27, 2127. <http://dx.doi.org/10.1016/S0040-4039(00)84466-4>
  • Page Philip C.Bulman, Rayner Christopher M., Sutherland Ian O.: Stereospecific synthesis of exo- and endo-1,3-dimethyl-2,9-dioxabicyclo-[3.3.1]-nonane. Tetrahetron Lett 1986, 27, 3535. <http://dx.doi.org/10.1016/S0040-4039(00)84843-1>
  • Schlecht Matthew F., Kim Ho-jin: Substituent-directed oxidation: Transannular oxidative cyclization of cycloalkenols to β-keto cyclic ethers. Tetrahetron Lett 1986, 27, 4889. <http://dx.doi.org/10.1016/S0040-4039(00)85089-3>
  • Bryce Martin: Chiral chemistry: Asymmetric epoxidation gives organic chemists a hand. Appl Opt 1986, 322, 776. <http://dx.doi.org/10.1038/322776a0>
  • Schweiter M.J., Sharpless K.Barry: The asymmetric epoxidation of -butyl substituted allylic alcohols. Tetrahetron Lett 1985, 26, 2543. <http://dx.doi.org/10.1016/S0040-4039(00)98832-4>
  • McGarvey Glenn J., Kimura Masayuki, Oh Taeboem, Williams J. Michael: Acyclic Stereoselective Synthesis of Carbohydrates. J Carbohydr Chem 1984, 3, 125. <http://dx.doi.org/10.1080/07328308408058813>