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Pure Appl. Chem., 2002, Vol. 74, No. 1, pp. 167-174

http://dx.doi.org/10.1351/pac200274010167

Toward the understanding of the mechanism and enantioselectivity of the Pauson­Khand reaction. Theoretical and experimental studies

Miquel A. Pericàs, Jaume Balsells, Jaume Castro, Iolanda Marchueta, Albert Moyano, Antoni Riera, Jordi Vázquez and Xavier Verdaguer

Unitat de Recerca en Síntesi Asimètrica, Departament de Química Orgànica, Universitat de Barcelona, E-08028 Barcelona, Spain

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  • Fustero Santos, Lázaro Rubén, Aiguabella Nuria, Riera Antoni, Simón-Fuentes Antonio, Barrio Pablo: Asymmetric Allylation/Pauson–Khand Reaction: A Simple Entry to Polycyclic Amines. Application to the Synthesis of Aminosteroid Analogues. Org. Lett. 2014, 16, 1224. <http://dx.doi.org/10.1021/ol500142c>
  • Wilson Matthew R., Taylor Richard E.: Gespannte Moleküle in der Naturstoffsynthese. Angew. Chem. 2013, 125, 4170. <http://dx.doi.org/10.1002/ange.201207712>
  • Aiguabella Nuria, del Pozo Carlos, Verdaguer Xavier, Fustero Santos, Riera Antoni: Synthesis and Application of β-Substituted Pauson-Khand Adducts: Trifluoromethyl as a Removable Steering Group. Angew. Chem. 2013, 125, 5463. <http://dx.doi.org/10.1002/ange.201300907>
  • Wilson Matthew R., Taylor Richard E.: Strained Alkenes in Natural Product Synthesis. Angew. Chem. Int. Ed. 2013, 52, 4078. <http://dx.doi.org/10.1002/anie.201207712>
  • Aiguabella Nuria, del Pozo Carlos, Verdaguer Xavier, Fustero Santos, Riera Antoni: Synthesis and Application of β-Substituted Pauson-Khand Adducts: Trifluoromethyl as a Removable Steering Group. Angew. Chem. Int. Ed. 2013, 52, 5355. <http://dx.doi.org/10.1002/anie.201300907>
  • Asano Keisuke, Uesugi Yuki, Yoshida Jun-ichi: Pauson–Khand Reactions in a Photochemical Flow Microreactor. Org. Lett. 2013, 15, 2398. <http://dx.doi.org/10.1021/ol4008519>
  • Chen Gen-Qiang, Shi Min: Rhodium-catalyzed tandem Pauson–Khand type reactions of 1,4-enynes tethered by a cyclopropyl group. Chem. Commun. 2013, 49, 698. <http://dx.doi.org/10.1039/c2cc37587g>
  • Maestro Alicia, Pedrosa Rafael, Pérez-Encabo Alfonso, Pérez-Rueda Juan J.: (−)-8-Amino menthol-derived perhydrobenzoxazines as chiral templates and masked aldehydes in the diastereoselective intermolecular Pauson–Khand reaction. Tetrahedron 2012, 68, 9293. <http://dx.doi.org/10.1016/j.tet.2012.08.006>
  • Fager-Jokela Erika, Muuronen Mikko, Patzschke Michael, Helaja Juho: Electronic Regioselectivity of Diarylalkynes in Cobalt-Mediated Pauson–Khand Reaction: An Experimental and Computational Study with Para- and Meta-Substituted Diarylalkynes and Norbornene. J. Org. Chem. 2012, 77, 9134. <http://dx.doi.org/10.1021/jo3016902>
  • Fjermestad Torstein, Pericàs  Miquel A., Maseras  Feliu: A Computational Study on the Role of Chiral N-Oxides in Enantioselective Pauson-Khand Reactions. Chemistry A European Journal 2011, 17, 10050. <http://dx.doi.org/10.1002/chem.201101166>
  • Moulton Benjamin E., Whitwood Adrian C., Duhme-Klair Anne K., Lynam Jason M., Fairlamb Ian J. S.: Regiochemistry in Cobalt-Mediated Intermolecular Pauson–Khand Reactions of Unsymmetrical Internal Heteroaromatic Alkynes with Norbornene. J Org Chem 2011, 76, 5320. <http://dx.doi.org/10.1021/jo200664m>
  • Ferrer Catalina, Benet-Buchholz Jordi, Riera Antoni, Verdaguer Xavier: Phosphine-Alkene Ligands as Mechanistic Probes in the Pauson-Khand Reaction. Chem Eur J 2010, 16, 8340. <http://dx.doi.org/10.1002/chem.201000357>
  • Pericas Miquel A., Balsells Jaume, Castro Jaume, Marchueta Iolanda, Moyano Albert, Riera Antoni, Vazquez Jordi, Verdaguer Xavier: ChemInform Abstract: Toward the Understanding of Mechanism and Enantioselectivity of the Pauson-Khand Reaction: Theoretical and Experimental Studies. ChemInform 2010, 33, no. <http://dx.doi.org/10.1002/chin.200241270>
  • Antras Frédéric, Laurent Stéphane, Ahmar Mohammed, Chermette Henry, Cazes Bernard: Pauson-Khand Reaction of Allenic Hydrocarbons: Synthesis of 4-Alkylidenecyclopentenones. Eur J Org 2010, 2010, 3312. <http://dx.doi.org/10.1002/ejoc.200901224>
  • Moulton Benjamin E., Lynam Jason M., Duhme-Klair Anne-Kathrin, Zheng Wenxu, Lin Zhenyang, Fairlamb Ian J. S.: Atropisomerisation in sterically hindered α,β-disubstituted cyclopentenones derived from an intermolecular cobalt(0)-mediated Pauson–Khand reaction. Org Biomol Chem 2010, 8, 5398. <http://dx.doi.org/10.1039/c0ob00264j>
  • Le Marquand Paul, Tam William: Enantioselektive palladiumkatalysierte Trimethylenmethan-[3+2]-Cycloadditionen. Angew Chem 2008, 120, 2968. <http://dx.doi.org/10.1002/ange.200705481>
  • Le Marquand Paul, Tam William: Enantioselective Palladium-Catalyzed Trimethylenemethane [3+2] Cycloadditions. Angew Chem Int Ed 2008, 47, 2926. <http://dx.doi.org/10.1002/anie.200705481>
  • Kuznetsov M. L., Kukushkin V. Yu.: Theoretical investigation of cycloaddition reactions with Lewis acid mediation. Russ J Inorg Chem 2008, 53, 1997. <http://dx.doi.org/10.1134/S0036023608130020>
  • Gibson Susan E., Hardick David J., Haycock Peter R., Kaufmann Karina A. C., Miyazaki Ayako, Tozer Matthew J., White Andrew J. P.: A Study of (Binap)(enyne)tetracarbonyldicobalt(0) Complexes. Chem Eur J 2007, 13, 7099. <http://dx.doi.org/10.1002/chem.200700587>
  • Burton Ryan R., Tam William: Ruthenium-catalyzed [2+2] cycloadditions between C1-substituted 7-oxanorbornadienes and alkynes. Tetrahetron Lett 2006, 47, 7185. <http://dx.doi.org/10.1016/j.tetlet.2006.07.155>
  • Christoffers Jens, Baro Angelika: Stereoselective Construction of Quaternary Stereocenters. Adv Synth Catal 2005, 347, 1473. <http://dx.doi.org/10.1002/adsc.200505165>
  • Gibson Susan E., Mainolfi Nello: Die intermolekulare Pauson-Khand-Reaktion. Angew Chem 2005, 117, 3082. <http://dx.doi.org/10.1002/ange.200462235>
  • Gibson Susan E., Mainolfi Nello: The Intermolecular Pauson-Khand Reaction. Angew Chem Int Ed 2005, 44, 3022. <http://dx.doi.org/10.1002/anie.200462235>
  • Martín Nazario, Altable Margarita, Filippone Salvatore, Martín-Domenech Ángel, Poater Albert, Solà Miquel: Regioselective Intramolecular Pauson-Khand Reactions of C60: An Electrochemical Study and Theoretical Underpinning. Chem Eur J 2005, 11, 2716. <http://dx.doi.org/10.1002/chem.200401200>
  • Riddell Nicole, Villeneuve Karine, Tam William: Ruthenium-Catalyzed [2 + 2] Cycloadditions of Ynamides. Org Lett 2005, 7, 3681. <http://dx.doi.org/10.1021/ol0512841>
  • Pallerla Mahesh K., Fox Joseph M.: Diastereoselective Intermolecular Pauson−Khand Reactions of Chiral Cyclopropenes. Org Lett 2005, 7, 3593. <http://dx.doi.org/10.1021/ol051456u>
  • Rodríguez Rivero Marta, Alonso Inés, Carretero Juan C.: Vinyl Sulfoxides as Stereochemical Controllers in Intermolecular Pauson-Khand Reactions: Applications to the Enantioselective Synthesis of Natural Cyclopentanoids. Chem Eur J 2004, 10, 5443. <http://dx.doi.org/10.1002/chem.200400443>
  • Boñaga Llorente V.R., Krafft Marie E.: When the Pauson–Khand and Pauson–Khand type reactions go awry: a plethora of unexpected results. Tetrahedron 2004, 60, 9795. <http://dx.doi.org/10.1016/j.tet.2004.06.072>
  • Delerue Hélène, Queste Mathieu, Nowicki Audrey, Suisse Isabelle, Agbossou-Niedercorn Francine, Maerten Eddy: Catalytic asymmetric carbonylative silylcarbocyclization of enynes. Tet Asymm 2004, 15, 3019. <http://dx.doi.org/10.1016/j.tetasy.2004.08.019>
  • Villeneuve Karine, Riddell Nicole, Jordan Robert W., Tsui Gavin C., Tam William: Ruthenium-Catalyzed [2 + 2] Cycloadditions between Bicyclic Alkenes and Alkynyl Halides. Org Lett 2004, 6, 4543. <http://dx.doi.org/10.1021/ol048111g>