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[reaction: see text] Bipyridyl(pentamethylcyclopentadienyl)ruthenium chloride is an efficient catalyst for the formal [3,3] rearrangement of allyl beta-ketoesters. The mechanism of the transformation involves formation of pi-allyl ruthenium intermediates, which are selectively attacked at the more substituted allyl terminus by freely diffusing enolates. Decarboxylation of beta-ketocarboxylates allows generation of enolates under extremely mild conditions.
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Burger et al. (2004) studied this question.
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