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Synthesis 1992; 1992(10): 1018-1025
DOI: 10.1055/s-1992-26292
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3-Metallierte Enamine XI1 Transmetallierung 3-stannylierter Enamine2 - Eine neue Methode zur Herstellung von 1-Aminoallyllithium-Verbindungen

Hubertus Ahlbrecht* , Peter Weber
  • *Fachbereich Chemie der Universität Gießen, Institut für Organische Chemie, Heinrich-Buff-Ring 58, D-6300 Gießen, Germany
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Publikationsdatum:
17. September 2002 (online)

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3-Metallated Enamines XI1 Transmetallation of 3-Stannylated Enamines2 - a New Method to Generate 1-Aminoallyllithium Compounds The transmetallation of 3-stannylated enamines,3 1-morpholino-3-(trialkylstannyl)cycloalk-1-enes and 3-morpholino-5-(tributylstannyl)hex-3-ene, with butyllithium is a new and general way to generate 1-aminoallyllithium compounds. Stabilization by aromatic substituents is not further necessary as in the case of preparation by deprotonation and even the thermodynamically less stable exo- amino derivatives are accessible. Therefore homoenolate-equiva- lents of cyclic ketones are made available. Thus, the corresponding 3-alkylated or 3-silylated cycloalkanones and alken-3-ones were prepared via the 1-morpholinoallyllithium compounds.