Download PDF
Synthesis 1997; 1997(8): 917-920
DOI: 10.1055/s-1997-1273
paper
© 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.

Baeyer-Villiger Oxidation of 6-Oxotricyclo[3.2.1.02,7]octanes; Regioselective Opening of Push-Pull Substituted Cyclopropanes

Norbert A. Braun, Natascha Stumpf, Dietrich Spitzner*
  • *Institut für Chemie, Abt. Organische Chemie, Universität Hohenheim, Garbenstraße 30, D-70599 Stuttgart, Germany, Fax +49(711)4592951; E-mail: spitzner@uni-hohenheim.de
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

Cascade reactions of cyclic dienolates 1 with enantiopure Michael acceptors 2 lead to 3. Oxidation of 3 under Baeyer-Villiger conditions gave solely the lactones 4. The double-push-pull substituted cyclopropane moiety of 4a was selectively opened upon hydrogenolysis to yield oxabicyclo[3.3.1]nonane 6. Reduction of lactone 4a gave the hemiacetal 7. It was converted to the vinylcyclopropane 10 which was hydrogenated to give the highly functionalized cycloheptane 11 and oxabicyclo[3.2.1]octanes 12.

cascade reaction - Michael addition - Baeyer-Villiger oxidation - enantiopure oxatricyclo[3.3.1.04,6]nonanes