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Synthesis 1987; 1987(1): 1-9
DOI: 10.1055/s-1987-27826
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3-Alkoxyacroleins in Organic Synthesis

Eberhard Breitmaier* , Friedrich-Wilhelm Ullrich, Birgit Potthoff, Roswitha Böhme, Heinz Bastian
  • *Institut für Organische Chemie und Biochemie der Universität Bonn Gerhard-Domagk-Str. 1, D-5300 Bonn, West Germany
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Publikationsdatum:
20. August 2002 (online)

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3-Alkoxyacroleins are reviewed as useful C3 building blocks for cyclizations and C-C bond connections. They open pathways to a variety of heterocyclic systems with up to fourteen-membered rings and permit oxopropenylations of carbon nucleophiles, resulting in other versatile intermediates such as α,β-unsaturated aldehydes and 1-alkoxy-1,3-dienes. 1. Introduction 2. Synthesis of 3-Alkoxyacroleins 3. Aminolysis of 3-Alkoxyacroleins and Reactions of 3-Aminoacroleins 4. Cyclizations of 3-Alkoxyacroleins with Heterocyclic Enamines 5. Cyclizations with Amidines 6. Cyclizations with Hydrazines 7. Cyclizations with Enediamines 8. Reductive Coupling of 3-Ethoxyacroleins (McMurry Reaction) 9. Reactions with Carbon Nucleophiles 10. Reactions with Ylides