CrossRef enabled

PAC Archives

Archive →

Pure Appl. Chem., 1987, Vol. 59, No. 3, pp. 363-372

http://dx.doi.org/10.1351/pac198759030363

Vitamin B12-mediated electrochemical reactions in the synthesis of natural products

R. Scheffold, Stefan Abrecht, R. Orlinski, H.-R. Ruf, P. Stamouli, O. Tinembart, L. Walder and C. Weymuth

CrossRef Cited-by theme picture

CrossRef Cited-by Linking

  • Giedyk M., Fedosov S. N., Gryko D.: An amphiphilic, catalytically active, vitamin B12 derivative. Chem. Commun. 2014, 50, 4674. <http://dx.doi.org/10.1039/c4cc01064g>
  • Kumar Manoj, Galezowski Wlodzimierz, Kozlowski Pawel M.: Computational modeling of standard reduction potentials of B12 cofactors. Int. J. Quantum Chem. 2013, 113, 479. <http://dx.doi.org/10.1002/qua.24155>
  • Hoffmann Norbert: Homogeneous Photocatalytic Reactions with Organometallic and Coordination Compounds-Perspectives for Sustainable Chemistry. ChemSusChem 2012, 5, 352. <http://dx.doi.org/10.1002/cssc.201100286>
  • Aghapoor Kioumars, Mohsenzadeh Farshid, Talebian Shiva, Tehrani Mohammad Jafar, Balavar Yadollah, Khanalizadeh Golriz, Darabi Hossein Reza: Vitamin B1 as a metal-ion-free natural catalyst for sustainable quinoxaline ring condensation under sonochemical conditions. Monatshefte für Chemie 2011, 142, 619. <http://dx.doi.org/10.1007/s00706-011-0487-5>
  • Poonam, Kumari Pratibha, Ahmad Sohail, Chauhan Shive Murat Singh: Reductive dechlorination of atrazine using sodium-borohydride catalysed by cobalt(II) phthalocyanines. Tetrahedron Letters 2011, 52, 7083. <http://dx.doi.org/10.1016/j.tetlet.2011.10.080>
  • Kim Hyejin, Lee Chulbom: Nickel-Catalyzed Reductive Cyclization of Organohalides. Org Lett 2011, 13, 2050. <http://dx.doi.org/10.1021/ol200455n>
  • Nuthakki Bharathi, Rusling James F.: Electrochemical catalysis by crosslinked films of cobalt reconstituted myoglobin and poly(l-lysine) in a bicontinuous microemulsion. Journal of Electroanalytical Chemistry 2005, 581, 139. <http://dx.doi.org/10.1016/j.jelechem.2005.04.005>
  • Studer Armido: The Persistent Radical Effect in Organic Synthesis. Chem Eur J 2001, 7, 1159. <http://dx.doi.org/10.1002/1521-3765(20010316)7:6<1159::AID-CHEM1159>3.0.CO;2-I>
  • Zhang Wei: Intramolecular free radical conjugate additions. Tetrahedron 2001, 57, 7237. <http://dx.doi.org/10.1016/S0040-4020(01)00634-2>
  • Petrović Zorica, Mojsilović Biljana, Bugarčić Zorica M.: Vitamin B12-catalyzed conversion of some γ- and δ-bromoalkanols to polyhydroxy alkanols. Journal of Molecular Catalysis A 2001, 170, 267. <http://dx.doi.org/10.1016/S1381-1169(00)00557-4>
  • Lvov Yuri M., Kamau Geoffrey N., Zhou De-Ling, Rusling James F.: Assembly of Electroactive Ordered Multilayer Films of Cobalt Phthalocyanine Tetrasulfonate and Polycations. Journal of Colloid and Interface Science 1999, 212, 570. <http://dx.doi.org/10.1006/jcis.1998.6083>
  • Gao Jianxin, Njue Christopher K., Mbindyo Jeremiah K.N., Rusling James F.: Mechanism of stereoselective production of trans-1-decalone by electrochemical catalysis in microemulsions. Journal of Electroanalytical Chemistry 1999, 464, 31. <http://dx.doi.org/10.1016/S0022-0728(98)00463-X>
  • Alatorre Ordaz Alejandro, Bedioui Fethi: The electrocatalytic reduction of organohalides by myoglobin and hemoglobin in a biomembrane-like film and its application to the electrochemical detection of pollutants: new trends and discussion. Actuat B 1999, 59, 128. <http://dx.doi.org/10.1016/S0925-4005(99)00209-9>
  • Petrović Zorica, Bugarčić Zorica, Marjanović Ljiljana, Konstantinović Stanimir: Reductive B12-catalyzed transformation of some tetrachloroalkanols to cyclopropane alkanols. Journal of Molecular Catalysis A 1999, 142, 393. <http://dx.doi.org/10.1016/S1381-1169(99)00060-6>
  • Gao Jianxin, Rusling James F.: Electron transfer and electrochemical catalysis using cobalt-reconstituted myoglobin in a surfactant film. Journal of Electroanalytical Chemistry 1998, 449, 1. <http://dx.doi.org/10.1016/S0022-0728(98)00058-8>
  • Mayer Stanislas, Prandi Jacques, Bamhaoud Toufiq, Bakkas Salem, Guillou Olivier: Synthesis of perhydro-furo[2,3-b]pyran (and furan)-3-yl methanols by oxygenative radical cyclization. Tetrahedron 1998, 54, 8753. <http://dx.doi.org/10.1016/S0040-4020(98)00478-5>
  • Zagal J.H., Aguirre M.J., Páez M.A.: O2 reduction kinetics on a graphite electrode modified with adsorbed vitamin B12. Journal of Electroanalytical Chemistry 1997, 437, 45. <http://dx.doi.org/10.1016/S0022-0728(97)00253-2>
  • Rusling James F., Zhou De-Ling: Electrochemical catalysis in microemulsions. Dynamics and organic synthesis. Journal of Electroanalytical Chemistry 1997, 439, 89. <http://dx.doi.org/10.1016/S0022-0728(97)00374-4>
  • Hemamalini Sundarababu, Scheffold Rolf: Synthesis of (+)-Multifidene. HCA 1995, 78, 447. <http://dx.doi.org/10.1002/hlca.19950780215>
  • Hartung Jens, Hertel Barbara, Trach Frank: What is Different in Photochemical Reactions of Primary and Secondary Alkylcobaloximes with and without Radical Traps?. Chem Ber 1993, 126, 1187. <http://dx.doi.org/10.1002/cber.19931260519>
  • Giese Bernd, Kesselheim Christoph, Hartung Jens, Lindner Hans Jörg, Svoboda Ingrid: Preparation and Properties of Alkylbis(dimethylglyoximato)rhodium(III) Complexes. Chem Ber 1993, 126, 1193. <http://dx.doi.org/10.1002/cber.19931260520>
  • Auer Lucas, Weymuth Christophe, Scheffold Rolf: Vitamin-B12-Catalyzed C,C-Bond Formation. Synthesis of a california red scale pheromone. HCA 1993, 76, 810. <http://dx.doi.org/10.1002/hlca.19930760205>
  • Hart David J., Krishnamurthy Ramanarayanan, Pook Lori M., Seely Franklin L.: Bis(tri-n-butylstannyl)benzopinacolate: Preparation and use as a mediator of intermolecular free radical reactions. Tetrahetron Lett 1993, 34, 7819. <http://dx.doi.org/10.1016/S0040-4039(00)61484-3>
  • Izquierdo Isidoro, Rodríguez Miguel, Plaza Maria T., Vallejo Inmaculada: Stereoselective synthesis from D-glucose of (−)-∂-multistriatin (component of the European elm bark beetle, Scolytus multistriatus, aggregation pheromone). Tet Asymm 1993, 4, 2535. <http://dx.doi.org/10.1016/S0957-4166(00)82234-X>
  • Stupperich Erhard: Recent advances in elucidation of biological corrinoid functions. FEMS Microbiol Rev 1993, 12, 349. <http://dx.doi.org/10.1111/j.1574-6976.1993.tb00027.x>
  • Walder Lorenz, Steiger Beat: A Reduction Catalyst Powered by Its Own 10-Electron Battery: Synthesis and properties of a pentaviologen-linked corrinatocobalt complex. HCA 1992, 75, 90. <http://dx.doi.org/10.1002/hlca.19920750107>
  • Zhang Wei, Dowd Paul: A new free radical-based method for the synthesis of spiroannulated medium rings. Tetrahetron Lett 1992, 33, 3285. <http://dx.doi.org/10.1016/S0040-4039(00)92068-9>
  • Murakami Yukito, Hisaeda Yoshio, Kohno Hiroshi, Ohno Teruhisa, Nishioka Takuya: Hydrophobic Vitamin B12. XI. Preparation, Characterization, and Enantioselective Alkylation of Hydrophobic Vitamin B12 Bearing a Binaphthyl Moiety. Bull Chem Soc Jpn 1992, 65, 3094. <http://dx.doi.org/10.1246/bcsj.65.3094>
  • Lee Edward R., Lakomy Ivo, Bigler Peter, Scheffold Rolf: Reductive Radical Cyclisations of Bromo Acetals and (Bromomethyl)silyl Ethers of Terpenoid Alcohols. HCA 1991, 74, 146. <http://dx.doi.org/10.1002/hlca.19910740117>
  • Giese Bernd, Thoma Gebhard: CC Bond Formationvia Carbon-Centered Radicals Generated from Dicarbonyl(η5-cyclopentadienyl) organoiron Complexes. HCA 1991, 74, 1143. <http://dx.doi.org/10.1002/hlca.19910740524>
  • Bonhôte Pierre, Scheffold Rolf: Asymmetric Catalysis by Vitamin B12. The Mechanism of the Cob(I)alamin-Catalyzed Isomerization of 1,2-Epoxycyclopentane to (R)-Cyclopent-2-enol. HCA 1991, 74, 1425. <http://dx.doi.org/10.1002/hlca.19910740706>
  • Kräutler Bernhard: Photochemical reactions of vitamin B12 derivatives. Coord Chem Rev - 1991, 111, 215. <http://dx.doi.org/10.1016/0010-8545(91)84026-2>
  • Zhou De-Ling, Tinembart Olivier, Scheffold Rolf, Walder Lorenz: Influence of the Axial Alkyl Ligand on the Reduction Potential of Alkylcob(III)alamins and Alkylcob(III)yrinates. HCA 1990, 73, 2225. <http://dx.doi.org/10.1002/hlca.19900730820>
  • Busato Stephan, Tinembart Olivier, Zhang Zhong-da, Scheffold Rolf: Vitamin B129 a catalyst in the synthesis of prostaglandins. Tetrahedron 1990, 46, 3155. <http://dx.doi.org/10.1016/S0040-4020(01)85455-7>
  • STUPPERICH Erhard, EISINGER Hans Jurgen, ALBRACHT Simon P. J.: Evidence for a super-reduced cobamide as the major corrinoid fraction in vivo and a histidine residue as a cobalt ligand of the p-cresolyl cobamide in the acetogenic bacterium Sporomusa ovata. Eur J Biochem 1990, 193, 105. <http://dx.doi.org/10.1111/j.1432-1033.1990.tb19310.x>
  • Stupperich Erhard, Eisinger Hans-Jürgen, Schurr Sabine: Corrinoids in anaerobic bacteria. FEMS Microbiol Lett 1990, 87, 355. <http://dx.doi.org/10.1111/j.1574-6968.1990.tb04936.x>
  • Giese Bernd, Hartung Jens, He Jianing, Hüter Ottmar, Koch Andreas: Zum Auftreten „freier Radikale” aus Alkylcobalt-Komplexen. Angew Chem 1989, 101, 334. <http://dx.doi.org/10.1002/ange.19891010320>
  • Giese Bernd, Hartung Jens, He Jianing, Hüter Ottmar, Koch Andreas: On the Formation of “Free Radicals” from Alkylcobalt Complexes. Angew Chem Int Ed Engl 1989, 28, 325. <http://dx.doi.org/10.1002/anie.198903251>
  • Wershofen Stefan, Claßen Arnold, Scharf Hans-Dieter: Stereoselektive Acetalisierung von 1,1- und 1,2-disubstituierten Diolen als allgemeines Syntheseprinzip für die Enantiomeren der bicyclischen Acetalpheromoneendo- undexo-Brevicomin sowie Frontalin. Liebigs Ann Chem 1989, 1989, 9. <http://dx.doi.org/10.1002/jlac.198919890104>
  • Mikolaiski Wolfgang, Baum Gerhard, Massa Werner, Hoffmann Reinhard W.: Bildung und Struktur von Allylperoxy-cobalt(III)-tetraphenyl-porphyrin. J Organomet Chem 1989, 376, 397. <http://dx.doi.org/10.1016/0022-328X(89)85149-6>
  • Thoma Gebhard, Giese Bernd: Generation and synthetic use of alkyl radicals with [CpFe(CO)2]2 as mediator. Tetrahetron Lett 1989, 30, 2907. <http://dx.doi.org/10.1016/S0040-4039(00)99155-X>
  • Tinembart Olivier, Walder Lorenz, Scheffold Rolf: Reductive Cleavage of the Co,C-Bond of [(Methoxycarbonyl)methyl]cobalamin. Berichte der Bunsengesellschaft für physikalische Chemie 1988, 92, 1225. <http://dx.doi.org/10.1002/bbpc.198800302>
  • Su Heng, Walder Lorenz, Zhang Zhong-da, Scheffold Rolf: Asymmetric Catalysis by Vitamin B12. The isomerization of achiral epoxides to optically active allylic alcohols. HCA 1988, 71, 1073. <http://dx.doi.org/10.1002/hlca.19880710520>
  • Scheffold Rolf: Vitamin B12 in der organischen Synthese. Nachr Chem Tech Lab 1988, 36, 261. <http://dx.doi.org/10.1002/nadc.19880360305>
  • Branchaud Bruce P., Meier Mark S., Choi Youngshin: Alkyl-alkenyl cross coupling via alkyl cobaloxime radical chemistry.An alkyl equivalent to the heck reaction compatible with common organic functional groups. Tetrahetron Lett 1988, 29, 167. <http://dx.doi.org/10.1016/S0040-4039(00)80043-X>
  • Orliński Ryszard, Stankiewicz Tomasz: Vitamin B12 photoelectrocatalysed (B12/PEC) synthesis of 2-aminoesters. Tetrahetron Lett 1988, 29, 1601. <http://dx.doi.org/10.1016/S0040-4039(00)80364-0>
  • Branchaud Bruce P., Choi Youngshin Lee: Effect of a remote ligand substituent on premature β-H elimination in a cobaloxime-mediated radical alkyl-alkenyl cross coupling. Tetrahetron Lett 1988, 29, 6037. <http://dx.doi.org/10.1016/S0040-4039(00)82258-3>
  • P.Branchaud Bruce, Yu Gui-Xue: Cobaloxime-mediated radical alkyl-nitroalkylanion cross coupling. Tetrahetron Lett 1988, 29, 6545. <http://dx.doi.org/10.1016/S0040-4039(00)82393-X>