A Simple Alkylative 1,2-Carbonyl Transposition of Cyclohexenones |
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Authors: | Wolfgang Oppolzer Tarun Sarkar Kumar K. Mahalanabis |
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Abstract: | Acid catalysed dehydration of the diols 5 , derived from the cyclohexenone 3 affords mixtures of 8 and 11 . The product ratio 8/11 , although strongly dependent on both the reaction conditions and the substituent R, is independent of the diol configuration; this indicates a cationic intermediate 6 . Conditions were found, which allow the sequence A → B → C → D (Scheme 2) to be applied to the syntheses of the enones 8, 21 and 25 in fair to good yields from the corresponding cyclohexenones 3, 18 and 22 . |
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