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Pure Appl. Chem., 2006, Vol. 78, No. 2, pp. 469-476

http://dx.doi.org/10.1351/pac200678020469

Connecting catalytic cycles by organometallic transformations in situ: Novel perspectives in the olefin metathesis field

Bernd Schmidt

Department of Chemistry, Organic Chemistry, University of Dortmund, Otto-Hahn-Strasse 6, D-44227 Dortmund, Germany

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  • Kadyrov Renat: Low Catalyst Loading in Ring-Closing Metathesis Reactions. Chem. Eur. J. 2013, 19, 1002. <http://dx.doi.org/10.1002/chem.201202207>
  • Takagi Ryukichi, Yamamoto Koumei, Hiraga Yoshikazu, Kojima Satoshi, Abe Manabu: A novel non-metathetic behavior of Grubbs catalyst: Ruthenium-mediated intramolecular [3 + 2] cycloaddition of bis-1,3-dienes. Journal of Organometallic Chemistry 2013, 723, 171. <http://dx.doi.org/10.1016/j.jorganchem.2012.09.004>
  • Taher Abu, Aderibigbe Blessing A., Morgans Garreth L., Madeley Lee G., Khanye Setshaba D., van der Westhuizen Leandi, Fernandes Manuel A., Smith Vincent J., Michael Joseph P., Green Ivan R., van Otterlo Willem A.L.: A ring-closing metathesis approach to eight-membered benzannelated scaffolds and subsequent internal alkene isomerizations. Tetrahedron 2013, 69, 2038. <http://dx.doi.org/10.1016/j.tet.2012.12.043>
  • Ashikari Yosuke, Shimizu Akihiro, Nokami Toshiki, Yoshida Jun-ichi: Halogen and Chalcogen Cation Pools Stabilized by DMSO. Versatile Reagents for Alkene Difunctionalization. J. Am. Chem. Soc. 2013, 135, 16070. <http://dx.doi.org/10.1021/ja4092648>
  • Schmidt Bernd, Krehl Stefan, Hauke Sylvia: Assisted Tandem Catalytic Cross Metathesis–Oxidation: In One Flask from Styrenes to 1,2-Diketones and Further to Quinoxalines. J. Org. Chem. 2013, 78, 5427. <http://dx.doi.org/10.1021/jo4005684>
  • Petersen Mette T., Nielsen Thomas E.: Tandem Ring-Closing Metathesis/Isomerization Reactions for the Total Synthesis of Violacein. Org. Lett. 2013, 15, 1986. <http://dx.doi.org/10.1021/ol400654r>
  • Schmidt Bernd, Hauke Sylvia: Cross metathesis of allyl alcohols: how to suppress and how to promote double bond isomerization. Org. Biomol. Chem. 2013, 11, 4194. <http://dx.doi.org/10.1039/c3ob40167g>
  • Ashikari Yosuke, Nokami Toshiki, Yoshida Jun-ichi: Integration of electrooxidative cyclization and chemical oxidation via alkoxysulfonium ions. Synthesis of exocyclic ketones from alkenes with cyclization. Org. Biomol. Chem. 2013, 11, 3322. <http://dx.doi.org/10.1039/c3ob40315g>
  • Mishra Priya, Singh Sarita, Ankit Preyas, Fatma Shahin, Singh Divya, Singh Jagdamba: Novel Synthesis of 3-Phenyl-chromen-4-ones Using N-Heterocyclic Carbene as Organocatalyst: An Efficient Domino Catalysis Type Approach. Bulletin of the Korean Chemical Society 2013, 34, 1070. <http://dx.doi.org/10.5012/bkcs.2013.34.4.1070>
  • Schmidt Bernd, Kunz Oliver: One-Flask Tethered Ring Closing Metathesis-Electrocyclic Ring Opening for the Highly Stereoselective Synthesis of Conjugated Z/E-Dienes. Eur J Org 2012, 2012, 1008. <http://dx.doi.org/10.1002/ejoc.201101497>
  • Ashikari Yosuke, Nokami Toshiki, Yoshida Jun-ichi: Oxidative Hydroxylation Mediated by Alkoxysulfonium Ions. Org Lett 2012, 14, 938. <http://dx.doi.org/10.1021/ol203467v>
  • Schmidt Bernd, Krehl Stefan, Jablowski Eric: Assisted tandem catalytic RCM-aromatization in the synthesis of pyrroles and furans. Org. Biomol. Chem. 2012, 10, 5119. <http://dx.doi.org/10.1039/c2ob25543j>
  • Ascic Erhad, Jensen Jakob F., Nielsen Thomas E.: Synthesis of Heterocycles through a Ruthenium-Catalyzed Tandem Ring-Closing Metathesis/Isomerization/N-Acyliminium Cyclization Sequence. Angew Chem 2011, 123, 5294. <http://dx.doi.org/10.1002/ange.201100417>
  • Ascic Erhad, Jensen Jakob F., Nielsen Thomas E.: Synthesis of Heterocycles through a Ruthenium-Catalyzed Tandem Ring-Closing Metathesis/Isomerization/N-Acyliminium Cyclization Sequence. Angew Chem Int Ed 2011, 50, 5188. <http://dx.doi.org/10.1002/anie.201100417>
  • Ding Fu, Doorslaer Sabine Van, Cool Peggie, Verpoort Francis: Olefin isomerization reactions catalyzed by ruthenium hydrides bearing Schiff base ligands. Appl Organometal Chem 2011, 25, 601. <http://dx.doi.org/10.1002/aoc.1808>
  • Ashikari Yosuke, Nokami Toshiki, Yoshida Jun-ichi: Integrated Electrochemical–Chemical Oxidation Mediated by Alkoxysulfonium Ions. J Am Chcm Soc 2011, 133, 11840. <http://dx.doi.org/10.1021/ja202880n>
  • Schmidt Bernd, Krehl Stefan: A single precatalyst tandem RCM–allylic oxidation sequence. Chem Commun 2011, 47, 5879. <http://dx.doi.org/10.1039/c1cc11347j>
  • Brown Lindsay, McGonagle Fiona I., Cooke Andrew, Sutherland Andrew: A three-step tandem process for the synthesis of bicyclic γ-lactams. Org Biomol Chem 2010, 8, 3418. <http://dx.doi.org/10.1039/c004695g>
  • Song Ren-Jie, Liu Yu, Li Rong-Jiang, Li Jin-Heng: Selective synthesis of 3-methyleneindolin-2-ones by one-pot multicatalytic processes. Tetrahetron Lett 2009, 50, 3912. <http://dx.doi.org/10.1016/j.tetlet.2009.04.066>
  • Rowley Christopher N., Woo Tom K.: Computational design of ruthenium hydride olefin-hydrogenation catalysts containing hemilabile ligands1,2. Can J Chem 2009, 87, 1030. <http://dx.doi.org/10.1139/V09-077>
  • Plumet Joaquín, Aljarilla Ana: Tandem Metathesis Reactions Cascade Ring-Opening Metathesis (ROM)-Ring-Closing Metathesis (RCM)-Cross Metathesis Dimerization (CMD) in 7-Oxabicyclo[2.2.1]hept-5-one (7-Oxanorbornene) Derivatives. HETEROCYCLES 2009, 77, 1333. <http://dx.doi.org/10.3987/COM-08-S(F)45>
  • Leogane Olivier, Lebel Hélène: One-Pot Multicomponent Synthesis of Indoles from 2-Iodobenzoic Acid. Angew Chem 2008, 120, 356. <http://dx.doi.org/10.1002/ange.200703671>
  • Leogane Olivier, Lebel Hélène: One-Pot Multicomponent Synthesis of Indoles from 2-Iodobenzoic Acid. Angew Chem Int Ed 2008, 47, 350. <http://dx.doi.org/10.1002/anie.200703671>
  • Schmidt Bernd, Biernat Anne: The Tandem Ring‐Closing Metathesis–Isomerization Approach to 6‐Deoxyglycals. Chem Eur J 2008, 14, 6135. <http://dx.doi.org/10.1002/chem.200800567>
  • Schmidt Bernd, Biernat Anne: Synthesis of 3-Deoxy Glycals via Tandem Metathesis Sequences and Their Use in an Intermolecular Heck Arylation. Eur J Org Chem 2008, 2008, 5764. <http://dx.doi.org/10.1002/ejoc.200800824>
  • Murelli Ryan P., Catalán Silvia, Gannon Michael P., Snapper Marc L.: Ruthenium-catalyzed tandem enyne-cross metathesis–cyclopropanation: three-component access to vinyl cyclopropanes. Tetrahetron Lett 2008, 49, 5714. <http://dx.doi.org/10.1016/j.tetlet.2008.07.119>
  • Appukkuttan Prasad, Dehaen Wim, Van der Eycken Erik: Microwave-Assisted Transition-Metal-Catalyzed Synthesis of N-Shifted and Ring-Expanded Buflavine Analogues. Chem Eur J 2007, 13, 6452. <http://dx.doi.org/10.1002/chem.200700177>
  • Schmidt Bernd: Connecting Catalytic Cycles by Organometallic Transformations in situ: Novel Perspectives in Olefin Metathesis. ChemInform 2006, 37. <http://dx.doi.org/10.1002/chin.200630277>
  • Schmidt Bernd, Staude Lucia: Unexpected transfer hydrogenation of C–C-double bonds during Tandem-RCM-isomerization reactions. J Organomet Chem 2006, 691, 5218. <http://dx.doi.org/10.1016/j.jorganchem.2006.07.011>
  • Dragutan Valerian, Dragutan Ileana: A resourceful new strategy in organic synthesis: Tandem and stepwise metathesis/non-metathesis catalytic processes. J Organomet Chem 2006, 691, 5129. <http://dx.doi.org/10.1016/j.jorganchem.2006.08.012>
  • Edlin Chris D., Faulkner James, Fengas David, Helliwell Madeleine, Knight Christopher K., House David, Parker Jeremy, Preece Ian, Quayle Peter, Raftery James: Toward catalyst economy: A programmed approach to the synthesis of bicyclic lactones and lactams. J Organomet Chem 2006, 691, 5375. <http://dx.doi.org/10.1016/j.jorganchem.2006.08.017>
  • Coyanis E. Mabel, Panayides Jenny-Lee, Fernandes Manuel A., de Koning Charles B., van Otterlo Willem A.L.: Ring-closing metathesis for the synthesis of substituted indenols, indenones, indanones and indenes: Tandem RCM-dehydrogenative oxidation and RCM-formal redox isomerization. J Organomet Chem 2006, 691, 5222. <http://dx.doi.org/10.1016/j.jorganchem.2006.08.074>