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Pure Appl. Chem., 2006, Vol. 78, No. 10, pp. 1857-1866

http://dx.doi.org/10.1351/pac200678101857

Synthesis of fine chemicals by the conjugate addition of nitroalkanes to electrophilic alkenes

R. Ballini, L. Barboni, G. Bosica, D. Fiorini and A. Palmieri

Dipartimento di Scienze Chimiche dell'Università di Camerino, Via S. Agostino 1, 62032 Camerino, Italy

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  • Bratko Ielyzaveta, Guisado-Barrios Gregorio, Favier Isabelle, Mallet-Ladeira Sonia, Teuma Emmanuelle, Peris Eduardo, Gómez Montserrat: Triazolium Salts as Appropriate Catalytic Scaffolds for 1,4-Additions to α,β-Unsaturated Carbonyls. Eur. J. Org. Chem. 2014, n/a. <http://dx.doi.org/10.1002/ejoc.201301220>
  • Ballini Roberto, Gabrielli Serena, Palmieri Alessandro: 1,3-Dinitro Alkanes: An Emerging Class of Bidentate Compounds. Eur. J. Org. Chem. 2014, 2014, 1805. <http://dx.doi.org/10.1002/ejoc.201301531>
  • Guideri Luca, De Sarlo Francesco, Machetti Fabrizio: Conjugate Addition versus Cycloaddition/Condensation of Nitro Compounds in Water: Selectivity, Acid-Base Catalysis, and Induction Period. Chem. Eur. J. 2013, 19, 665. <http://dx.doi.org/10.1002/chem.201202698>
  • Bielski Roman, Witczak Zbigniew: Strategies for Coupling Molecular Units if Subsequent Decoupling Is Required. Chem. Rev. 2013, 113, 2205. <http://dx.doi.org/10.1021/cr200338q>
  • Li Ya-Min, Wei Xiao-Hong, Li Xi-An, Yang Shang-Dong: Metal-free carbonitration of alkenes using K2S2O8. Chem. Commun. 2013, 49, 11701. <http://dx.doi.org/10.1039/c3cc47287f>
  • Mancuso Raffaella, Palmieri Alessandro, Ballini Roberto, Gabriele Bartolo: Base-free conjugate addition of aliphatic nitro compounds to enones in BmimNTf2: a recyclable synthesis of γ-nitro ketones. Tetrahedron 2012, 68, 5852. <http://dx.doi.org/10.1016/j.tet.2012.05.024>
  • Mondal Rina, Gupta Arpita Das, Mallik Asok K.: Synthesis of flavanones by use of anhydrous potassium carbonate as an inexpensive, safe, and efficient basic catalyst. Tetrahedron Letters 2011, 52, 5020. <http://dx.doi.org/10.1016/j.tetlet.2011.07.072>
  • López-García M. Ángeles, Maya Inés, Fernández-Bolaños José G., Bosica Giovanna, Ballini Roberto: 1-Alkoxyamino-2-nitroalkanes as Key Building Blocks for a Chemo- and Diastereoselective Synthesis of a New Type of Polyfunctionalized N-Alkoxypiperidine. Eur J Org Chem 2010, 2010, 5482. <http://dx.doi.org/10.1002/ejoc.201000540>
  • Shanbhag Pramod, Nareddy Pradeep R., Dadwal Mamta, Mobin Shaikh M., Namboothiri Irishi N. N.: Rauhut–Currier type homo- and heterocouplings involving nitroalkenes and nitrodienes. Org Biomol Chem 2010, 8, 4867. <http://dx.doi.org/10.1039/c0ob00062k>
  • Trogu Elena, De Sarlo Francesco, Machetti Fabrizio: Michael Additions versus Cycloaddition Condensations with Ethyl Nitroacetate and Electron-Deficient Olefins. Chem Eur J 2009, 15, 7940. <http://dx.doi.org/10.1002/chem.200802652>
  • Deb Indubhusan, Shanbhag Pramod, Mobin Shaikh M., Namboothiri Irishi N. N.: Morita-Baylis-Hillman Reactions Between Conjugated Nitroalkenes or Nitrodienes and Carbonyl Compounds. Eur J Org Chem 2009, 2009, 4091. <http://dx.doi.org/10.1002/ejoc.200900475>
  • Sośnicki Jacek G.: Michael addition of nitroalkanes to nonactivated α,β-unsaturated δ-thiolactams: reactivity, diastereoselectivity, and comparison to α,β-unsaturated δ-lactams. Tetrahedron 2009, 65, 1336. <http://dx.doi.org/10.1016/j.tet.2008.12.037>
  • Ballini R., Barboni L., Bosica G., Fiorini D., Palmieri A.: Synthesis of Fine Chemicals by the Conjugate Addition of Nitroalkanes to Electrophilic Alkenes. ChemInform 2007, 38. <http://dx.doi.org/10.1002/chin.200710274>
  • Rai Vishal, Mobin Shaikh M., Namboothiri Irishi N.N.: Cinchonine catalyzed diastereo- and enantioselective Michael addition of α-lithiated phosphonates to nitroalkenes. Tet Asymm 2007, 18, 2719. <http://dx.doi.org/10.1016/j.tetasy.2007.11.001>