196614-83-2Relevant academic research and scientific papers
Baeyer-Villiger oxidation of 6-oxotricyclo-[3.2.1.02,7]octanes; Regioselective opening of push-pull substituted cyclopropanes
Braun, Norbert A.,Stumpf, Natascha,Spitzner, Dietrich
, p. 917 - 920 (2007/10/03)
Cascade reactions of cyclic dienolates 1 with enantiopure Michael accepters 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 cycleheptane 11 and oxabicyclo[3.2.1]octanes 12.
