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Synthesis 1989; 1989(11): 820-824
DOI: 10.1055/s-1989-27401
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Cyclopropene als C3-Synthesebausteine: Cyclopentenole und große Ringe aus 2-Aminobicyclo[2.1.0]pentan-Derivaten über Ringerweiterungsreaktionen

Michel Franck-Neumann* , Michel Miesch, Hubert Kempf
  • *Unité de Recherche Associée au CNRS no 466, Institut de Chimie de l'Université Louis Pasteur, 1, rue Blaise Pascal, F-67008 France
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Publication Date:
02 May 2002 (online)

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Cyclopropenes as C3 Building Blocks: Cyclopentenols and Large Rings from 2-Aminobicyclo[2.1.0]pentane Derivatives via Ring-Enlargement Reactions The readily available methyl 3,3-dimethylcyclopropane-1-carboxylate undergoes [2+2] cycloaddition with enamines to give 2-aminobicyclo[2.1.0]pentane derivatives in moderate to good yields. These compounds are quantitatively transformed into 3-cyclopentenols by treatment with dilute mineral acids. From enamines derived from medium-ring ketones and morpholine, tricyclic adducts are formed, which eliminate morpholine under flash-thermolysis conditions at 600°C to give macrocycles containing an E double bond and an allenic system.