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Pure Appl. Chem., 2008, Vol. 80, No. 5, pp. 913-927

http://dx.doi.org/10.1351/pac200880050913

New preparative methods for allylic boronates and their application in stereoselective catalytic allylborations

Dennis G. Hall

Department of Chemistry, University of Alberta, Edmonton, AB, T6G 2G2, Canada

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  • Bhakta Urmibhusan, Sullivan Erin, Hall Dennis G.: Catalytic enantioselective allylboration of propargylic aldehydes. Tetrahedron 2014, 70, 678. <http://dx.doi.org/10.1016/j.tet.2013.11.095>
  • Hansmann Max M., Melen Rebecca L., Rominger Frank, Hashmi A. Stephen K., Stephan Douglas W.: Activation of Alkynes with B(C6F5)3 – Boron Allylation Reagents Derived from Propargyl Esters. J. Am. Chem. Soc. 2014, 136, 777. <http://dx.doi.org/10.1021/ja4110842>
  • Melen Rebecca L.: Applications of pentafluorophenyl boron reagents in the synthesis of heterocyclic and aromatic compounds. Chem. Commun. 2014, 50, 1161. <http://dx.doi.org/10.1039/c3cc48036d>
  • Incerti-Pradillos Celia A., Kabeshov Mikhail A., Malkov Andrei V.: Highly Stereoselective Synthesis of Z -Homoallylic Alcohols by Kinetic Resolution of Racemic Secondary Allyl Boronates. Angew. Chem. 2013, 125, 5446. <http://dx.doi.org/10.1002/ange.201300709>
  • Incerti-Pradillos Celia A., Kabeshov Mikhail A., Malkov Andrei V.: Highly Stereoselective Synthesis of Z -Homoallylic Alcohols by Kinetic Resolution of Racemic Secondary Allyl Boronates. Angew. Chem. Int. Ed. 2013, 52, 5338. <http://dx.doi.org/10.1002/anie.201300709>
  • Albury Aymara M.M., Jennings Michael P.: TiCl4 mediated preparation of (E)-non-conjugated homoallylic alcohols with α-substituted allylsilanes. Tetrahedron Letters 2013, 54, 4487. <http://dx.doi.org/10.1016/j.tetlet.2013.06.047>
  • Larsson Johanna M., Szabó Kálmán J.: Mechanistic Investigation of the Palladium-Catalyzed Synthesis of Allylic Silanes and Boronates from Allylic Alcohols. J. Am. Chem. Soc. 2013, 135, 443. <http://dx.doi.org/10.1021/ja309860h>
  • Macé Aurélie, Tripoteau Fabien, Zhao Qian, Gayon Eric, Vrancken Emmanuel, Campagne Jean-Marc, Carboni Bertrand: Tandem Reactions Involving 1-Silyl-3-Boryl-2-Alkenes. New Access to (Z)-1-Fluoro-1-Alkenes, Allyl Fluorides, and Diversely α-Substituted Allylboronates. Org. Lett. 2013, 15, 906. <http://dx.doi.org/10.1021/ol4000263>
  • Touchet Sabrina, Macé Aurélie, Roisnel Thierry, Carreaux François, Bouillon Alexandre, Carboni Bertrand: [3,3]-Sigmatropic Rearrangement of Boronated Allylcyanates: A New Route to α-Aminoboronate Derivatives and Trisubstituted Tetrahydrofurans. Org. Lett. 2013, 15, 2712. <http://dx.doi.org/10.1021/ol401016x>
  • Kliman Laura T., Mlynarski Scott N., Ferris Grace E., Morken James P.: Catalytic Enantioselective 1,2-Diboration of 1,3-Dienes: Versatile Reagents for Stereoselective Allylation. Angew. Chem. 2012, 124, 536. <http://dx.doi.org/10.1002/ange.201105716>
  • Kliman Laura T., Mlynarski Scott N., Ferris Grace E., Morken James P.: Catalytic Enantioselective 1,2-Diboration of 1,3-Dienes: Versatile Reagents for Stereoselective Allylation. Angew. Chem. Int. Ed. 2012, 51, 521. <http://dx.doi.org/10.1002/anie.201105716>
  • Blevins David W., Yao Min-Liang, Yong Li, Kabalka George W.: Iron trichloride promoted hydrolysis of potassium organotrifluoroborates. Tetrahedron Letters 2011, 52, 6534. <http://dx.doi.org/10.1016/j.tetlet.2011.09.140>
  • Hong Kai, Morken James P.: Catalytic Enantioselective Diboration of Cyclic Dienes. A Modified Ligand with General Utility. J Org Chern 2011, 76, 9102. <http://dx.doi.org/10.1021/jo201321k>
  • Canterbury Daniel P., Micalizio Glenn C.: Polyketide Assembly by Alkene−Alkyne Reductive Cross-Coupling: Spiroketals through the Union of Homoallylic Alcohols. J Am Chem Soc 2010, 132, 7602. <http://dx.doi.org/10.1021/ja102888f>
  • Hall Dennis G.: ChemInform Abstract: New Preparative Methods for Allylic Boronates and Their Application in Stereoselective Catalytic Allylborations. ChemInform 2008, 39. <http://dx.doi.org/10.1002/chin.200843249>