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Synlett 1996; 1996(1): 34-36
DOI: 10.1055/s-1996-5305
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Cationic 2-Azabutadienes from α-Arylaminosulfones and α-Arylaminonitriles: Intermolecular Polar [4π++2π]-Cycloadditions for the Regio- and Diastereoselective Synthesis of 1,2,3,4-Tetrahydroquinolines

Uwe Beifuss* , Olaf Kunz, Sabine Ledderhose, Michael Taraschewski, Christiane Tonko
  • *Institut für Organische Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, D-37077 Göttingen, Germany, Fax +49(551)39-9660
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Publication Date:
31 December 2000 (online)

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The intermolecular polar [4π+ + 2π]-cycloaddition of cationic 2-azabutadienes, which are generated in situ from α-arylaminosulfones and α-arylaminonitriles, respectively, with different dienophiles regio- and diastereoselectively yield 1,2,3,4-tetrahydroquinolines with yields from 66 to 92%.

α-Arylaminosulfone - α-Arylaminonitrile - 2-Azabutadiene - Polar Cycloaddition - 1,2,3,4-Tetrahydroquinoline

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