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Synthesis 1997; 1997(8): 917-920
DOI: 10.1055/s-1997-1273
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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
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Publikationsdatum:
31. Dezember 2000 (online)

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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