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Synlett 1995; 1995(12): 1223-1225
DOI: 10.1055/s-1995-5234
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An Efficient One-Pot Synthesis of Functionalized Cyclodecenone Derivatives from Siloxycyclopropanes

Jürgen Schnaubelt, Astrid Ullmann, Hans-Ulrich Reissig*
  • *Institut für Organische Chemie der Technischen Universität Dresden, Mommsenstrasse 13, D-01062 Dresden, Germany, Telefax: (internat.) +49(0)351/463-7030, E-mail: reissig@coch01.chm.tu-dresden.de
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Publication Date:
31 December 2000 (online)

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By straightforward steps siloxycyclopropanes 1a-1c were converted into compounds 3a-3c and 8a-c, respectively. Fluoride induced ring enlargement successfully proceeds with 3a, 3b, 8a, and 8c affording functionalized cyclodecenone derivatives 4a, 4b, 9a, and 9c. This one-pot procedure involves ring opening of the siloxycyclopropanes followed by intramolecular Michael additions.

Siloxycyclopropane carboxylates - Alkylation - Desilylation - Michael Addition intramolecular - Cyclodecenone Derivatives