… of 2, 2??Disubstituted Cyclopentane??1, 3??diones, 6. Conversion of 2??Methylcyclopentane??1, 3??dione into 5??Methylcycloheptane??1, 4??dione via 3??(1??Methyl??2, 5?? …

…, H Schwarz, A Hauser, S Schwarz

Index: Schick, Hans; Roatsch, Birgit; Schwarz, Hartmut; Hauser, Andre; Schwarz, Sigfrid Liebigs Annalen der Chemie, 1992 , # 5 p. 419 - 422

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Citation Number: 11

Abstract

Abstract In contrast to earlier reported unsuccessful experiments the Michael addition of prop-2-enal to 2-methylcyclopentane-1, 3-dione (1) affords 3-(1-methyl-2, 5- dioxocyclopentyl) propanal (3) in 90% yield, if the reaction is carried out in water without a basic catalyst. This aldehyde is converted by an intramolecular aldol reaction to (±)-endo-2- and (±)-exo-2-hydroxy-5-methylbicyclo [3.2. 1] octane-6, 8-dione (rac-4 and rac-6), both ...