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Pure Appl. Chem., 1990, Vol. 62, No. 10, pp. 2047-2056

http://dx.doi.org/10.1351/pac199062102047

The directed ortho metalation reaction. Methodology, applications, synthetic links, and a non-aromatic ramification

V. Snieckus

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  • Kacem Yakdhane, Hassine Béchir Ben: A new procedure for the synthesis of 4-substituted-2H-1,2,3-benzothiadiazine 1,1-dioxides via directed ortho-lithiation of N1-arylsulfonylhydrazonates. Tetrahedron Letters 2013, 54, 4023. <http://dx.doi.org/10.1016/j.tetlet.2013.05.082>
  • Essig Sebastian, Bretzke Sebastian, Müller Rolf, Menche Dirk: Full Stereochemical Determination of Ajudazols A and B by Bioinformatics Gene Cluster Analysis and Total Synthesis of Ajudazol B by an Asymmetric Ortholithiation Strategy. J. Am. Chem. Soc. 2012, 134, 19362. <http://dx.doi.org/10.1021/ja309685n>
  • Fournier Anne M., Clayden Jonathan: Tertiary Alcohols by Tandem β-Carbolithiation and N→C Aryl Migration in Enol Carbamates. Org Lett 2012, 14, 142. <http://dx.doi.org/10.1021/ol2029355>
  • SNIECKUS V.: ChemInform Abstract: The Directed Ortho Metalation Reaction: Methodology, Applications, Synthetic Links, and a Non-Aromatic Ramification. ChemInform 2010, 22, no. <http://dx.doi.org/10.1002/chin.199107310>
  • Bringmann Gerhard, Gulder Tanja, Hertlein Barbara, Hemberger Yasmin, Meyer Frank: Total Synthesis of the N,C-Coupled Naphthylisoquinoline Alkaloids Ancistrocladinium A and B and Related Analogues. J Am Chem Soc 2010, 132, 1151. <http://dx.doi.org/10.1021/ja9097687>
  • Kolodziejczyk Krzysztof, Roiban Gheorghe D., Schnürch Michael, Mihovilovic Marko D., Stanetty Peter: Synthesis of potential fungicides based on N-(3-furanyl)pyrrolecarboxamides and N-(3-furanyl)pyrazolecarboxamides. Monatshefte für Chemie 2009, 140, 1349. <http://dx.doi.org/10.1007/s00706-009-0187-6>
  • Fînaru Adriana-Luminita, Caubère Paul, Guillaumet Gérald, Grig-Alexa Irina-Claudia: Lithiation Directed by Amino Alkoxides. Application to the Synthesis of New Disubstituted Dihydrodipyridopyrazines. Org Lett 2006, 8, 4187. <http://dx.doi.org/10.1021/ol061178e>
  • Sahli Stefan, Stump Bernhard, Welti Tobias, Schweizer W. Bernd, Diederich François, Blum-Kaelin Denise, Aebi Johannes D., Böhm Hans-Joachim: A New Class of Inhibitors for the Metalloprotease Neprilysin Based on a Central Imidazole Scaffold. HCA 2005, 88, 707. <http://dx.doi.org/10.1002/hlca.200590050>
  • Zhang Tony Y., O'toole John, Proctor C. Scott: Recent Advances in the Synthesis and Applications of Benzo[b]thiophenes. Sulfur Reports 1999, 22, 1. <http://dx.doi.org/10.1080/01961779908047953>
  • Daia G.Elena, Gabbutt Christopher D., Hepworth John D., Heron B.Mark, Hibbs David E., Hursthouse Michael B.: The directed lithiation of some 3-acylchromone acetals. Tetrahetron Lett 1998, 39, 1215. <http://dx.doi.org/10.1016/S0040-4039(97)10733-X>
  • Hird Michael, Toyne Kenneth J.: Fluoro Substitution in Thermotropic Liquid Crystals. Molecular Crystals and Liquid Crystals Science and Technology Section A Molecular Crystals and Liquid Crystals 1998, 323, 1. <http://dx.doi.org/10.1080/10587259808048432>
  • Luh Tien-Yau: Chelation Assisted Conversion of C-S Bonds into C-C Bonds. Phosphorus Sulfur Silicon Relat Elem 1997, 120, 259. <http://dx.doi.org/10.1080/10426509708545523>
  • Hegedus Louis S.: Transition metals in organic synthesis annual survey covering the year 1990. J Organomet Chem 1992, 422, 301. <http://dx.doi.org/10.1016/0022-328X(92)88031-D>
  • J. Bridges Alexander, Lee Arthur, Maduakor Emmanuel C., Schwartz C.Eric: Fluorine as an ortho-directing group in aromatic metalation: Generality of the reaction and the high position of fluorine in the Dir-Met potency scale. Tetrahetron Lett 1992, 33, 7495. <http://dx.doi.org/10.1016/S0040-4039(00)60805-5>
  • Cabiddu Salvatore, Fattuoni Claudia, Floris Costantino, Gelli Gioanna, Melis Stefana, Cabiddu Maria G.: METALATION REACTIONS. PART XVII. DILITHIATION OF PHENYL ISOPROPYL SULPHONE. Phosphorus Sulfur Silicon Relat Elem 1992, 70, 139. <http://dx.doi.org/10.1080/10426509208049162>
  • Cabiddu Salvatore, Contini Liliana, Fattuoni Claudia, Floris Costantino, Gelli Gioanna: Metalation reactions. XVI. Polylithiation of 1,3,5- and 1,2,4-trimethoxybenzene. Tetrahedron 1991, 47, 9279. <http://dx.doi.org/10.1016/S0040-4020(01)96216-7>