Synlett 1995; 1995(4): 355-357
DOI: 10.1055/s-1995-4948
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

High Pressure Mediated Intramolecular Diels-Alder Reactions of Furans with Unactivated Methylenecyclopropane Terminators

Thomas Heiner, Stephan Michalski, Kerstin Gerke, Gabriele Kuchta, Michael Buback, Armin de Meijere*
  • *Institut für Organische Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2-6, D-37077 Göttingen, Germany
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
31. Dezember 2000 (online)

Furfuryl derivatives 3 with an allyl ether or allylamine type linkage to a methylenecyclopropane moiety readily undergo intramolecular Diels-Alder reactions at 10-12 kbar to yield interesting new spirocyclopropane-annelated tricyclic structures 4 diastereoselectively in excellent yields. The starting materials 3 are readily obtained by Pd0-catalysed nucleophilic allylic substitution on 1-chloro-1-ethenylcyclopropane 1 with furfurol or furfurylamine. Some acid-catalysed ring-openings of the 7’-methoxy derivative 4d are described as well. Furthermore, activation parameters for the intramolecular cycloaddition of 3a have been determined by means of on-line infrared spectroscopy under high pressure.