AdE2-Konsekutivreaktionen zur Eintopfsynthese polyfunktioneller Verbindungen

• Applicant: Professor Dr. Herbert Mayr
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2002 to 2006
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 5388370

• Final Report Year: 2006

Final Report Abstract

Methods for one-pot syntheses of highly functionalized organic compounds by consecutive additions of electrophiles and nucleophiles to 7i-systems have been developed through the collaboration of the groups of Professors loffe and Smit in Moscow and of Professor Mayr in München. Synthetic studies on sulfonium ion controlled reactions, electrophilic additions to N-siloxyenamines followed by nucleophilic additions of electronrich CC-double bonded compounds, and of successive electrophilic and nucleophilic additions to allyl-Fp complexes and isonitriles were complemented by kinetic investigations.

Publications

• Novel approach toward the preparation of 1,6-enynes - substrates for the intramolecular Pauson-Khand cyclization. Russian Chem. Bull. Int. Ed. 2003, 52, 2461-2466
  W. A. Smit, V. V. Tumanov, G. V. Zatonsky
  
• New C-C Coupling Reaction of Cyclic Nitronates with Carbon Nucleophiles. Umpolung of the Conventional Reactivity of Nitronates. J. Org. Chem. 2004, 69, 8485-8488
  V. O. Smirnov, S. L. Ioffe, A. A. Tishkov, Y. A. Khomutova, I. D. Nesterov, M. Y. Antipin, W. A. Smit, V. A. Tartakovsky
  
• On the conformational preferability of 5,6-dihydro-4-[H]-1,2-oxazines, their N-oxides and acyclic analogues. Mendeleev Commun. 2004,280-281
  I. D. Nesterov, A. V. Lesiv, S. L. Ioffe, M. Y. Antipin
  
• ArS-Mediated AdΕ Reaction of the Cobaltcarbonyl-Complexed Conjugated Enynes. Phosphorus, Sulfur, and Silicon 2005, 1279-1283
  V. V. Tumanov, W. A. Smit
  
• Quantification of the β-Stabilizing Effect of the Dicarbonyl(η5-cyclopentadienyl)iron Group. Helv. Chim. Acta 2005, 88, 1754- 1768
  F. Dulich, K.-H. Müller, A. R. Ofial, H. Mayr
  
• Reactions of ρ-toluenessulfenyl chloride with enol acetates. The synthetic potential of the resulting adducts. Russian Chem. Bull. Int. Ed. 2005, 54, 743-747
  W. A. Smit, E. A. Yagodkin, G. V. Zatonsky
  
• The Chemistry of N, N-Bis(siloxy)enamines, Part 8. A General Method for the Preparation of α-Azido Oximes from Aliphatic Nitro Compounds. Synthesis 2005, 7, 1077-1082
  A. Y. Sukhorokov, I. V. Bliznets, A. V. Lesiv, Y. A. Khomutova, Y. A. Strelenko, S. L. Ioffe
  
• The Chemistry of N, N-Bis(siloxy)enamines, Part 9. A General Method for the Preparation of α-Hydroxy Oximes from Aliphatic Nitro Compounds. Synthesis 2005, 70,1656-1662
  A. A. Tabolin, A. V. Lesiv, Y. A. Khomutova, P. A. Belyakov, Y, A. Strelenko, S. L. Ioffe
  
• β-Arylthio-α-chloroalkyl Ethers - Novel 1,1-Bis-electrophiles for Geminal Alkylation. Eur. J. Org, Chem. 2006, 1317-1322
  A. V. Gromov, W. A. Smit