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Pure Appl. Chem., 2004, Vol. 76, No. 3, pp. 625-633

http://dx.doi.org/10.1351/pac200476030625

New insights into the mechanism of molybdenum-catalyzed asymmetric alkylation

S. W. Krska, D. L. Hughes, R. A. Reamer, D. J. Mathre, M. Palucki, Nobuyoshi Yasuda, Y. Sun and B. M. Trost

Department of Process Research, Merck and Co., Inc., Rahway, NJ 07065, USA; Department of Chemistry, Stanford University, Palo Alto, CA 94305-5080, USA

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  • Lega Matteo, Figliolia Rosario, Moberg Christina, Ruffo Francesco: Expanding the scope of the elpaN-type library: glucose-derived bis(pyridine-2-carboxamide) ligands (elpaN-Py) for molybdenum-catalyzed asymmetric allylic alkylations. Tetrahedron 2013, 69, 4061. <http://dx.doi.org/10.1016/j.tet.2013.03.075>
  • Tosatti Paolo, Nelson Adam, Marsden Stephen P.: Recent advances and applications of iridium-catalysed asymmetric allylic substitution. Biomol Chem 2012, 10, 3147. <http://dx.doi.org/10.1039/c2ob07086c>
  • Trost Barry M., Zhang Yong: Molybdenum-Catalyzed Asymmetric Allylic Alkylation of 3-Alkyloxindoles: Reaction Development and Applications. Chem Eur J 2011, 17, 2916. <http://dx.doi.org/10.1002/chem.201002569>
  • Milheiro Suzanna C., Faller J.W.: Regioselectivity and memory effects in palladium catalyzed allylic alkylations with bidentate P^PS donor ligands. J Organomet Chem 2011, 696, 879. <http://dx.doi.org/10.1016/j.jorganchem.2010.10.022>
  • Trost Barry M., Miller John R., Hoffman Christopher M.: A Highly Enantio- and Diastereoselective Molybdenum-Catalyzed Asymmetric Allylic Alkylation of Cyanoesters. J Am Chem Soc 2011, 133, 8165. <http://dx.doi.org/10.1021/ja2029602>
  • Austeri Martina, Linder David, Lacour Jérôme: (Cyclopentadienyl)ruthenium-Catalyzed Regio- and Enantioselective Decarboxylative Allylic Etherification of Allyl Aryl and Alkyl Carbonates. Adv Synth Catal 2010, 352, 3339. <http://dx.doi.org/10.1002/adsc.201000696>
  • Del Litto Raffaella, Benessere Vincenzo, Ruffo Francesco, Moberg Christina: Carbohydrate-Based Pyridine-2-carboxamides for Mo-Catalyzed Asymmetric Allylic Alkylations. Eur J Org Chem 2009, 2009, 1352. <http://dx.doi.org/10.1002/ejoc.200801240>
  • Austeri Martina, Linder David, Lacour Jérôme: Enantioselective and Regioselective Ruthenium‐Catalyzed Decarboxylative Etherification of Allyl Aryl Carbonates. Chem Eur J 2008, 14, 5737. <http://dx.doi.org/10.1002/chem.200800619>
  • Linder David, Buron Frédéric, Constant Samuel, Lacour Jérôme: Enantioselective CpRu-Catalyzed Carroll Rearrangement - Ligand and Metal Source Importance. Eur J Org Chem 2008, 2008, 5778. <http://dx.doi.org/10.1002/ejoc.200800854>
  • Constant Samuel, Tortoioli Simone, Müller Jessica, Linder David, Buron Frédéric, Lacour Jérôme: Air- and Microwave-Stable (C5H5)Ru Catalysts for Improved Regio- and Enantioselective Carroll Rearrangements. Angew Chem 2007, 119, 9137. <http://dx.doi.org/10.1002/ange.200704019>
  • Constant Samuel, Tortoioli Simone, Müller Jessica, Linder David, Buron Frédéric, Lacour Jérôme: Air- and Microwave-Stable (C5H5)Ru Catalysts for Improved Regio- and Enantioselective Carroll Rearrangements. Angew Chem Int Ed 2007, 46, 8979. <http://dx.doi.org/10.1002/anie.200704019>
  • Luft Jennifer A.R., Yu Zhi-Xiang, Hughes David L., Lloyd-Jones Guy C., Krska Shane W., Houk Kendall N.: On the stability of the π-allyl intermediate in molybdenum-catalyzed asymmetric alkylations. Tet Asymm 2006, 17, 716. <http://dx.doi.org/10.1016/j.tetasy.2006.01.037>
  • Krska Shane W., Hughes David L., Reamer Robert A., Mathre David J., Palucki Michael, Yasuda Nobuyoshi, Sun Yongkui, Trost Barry M.: New Insights into the Mechanism of Molybdenum-Catalyzed Asymmetric Alkylation. ChemInform 2004, 35. <http://dx.doi.org/10.1002/chin.200437280>