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Medium-Sized Rings versus Macrocycles through Rhodium-Catalyzed Ring-Expansion Reactions of Cyclic Acetals

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Published in Chemistry - A European Journal. 2012, vol. 18, no. 21, p. 6626-6631
Abstract α-Diazo β-ketoesters and diketones react with cyclic acetals under RhII catalysis to yield unprecedented polyoxygenated 8- and 9-membered rings in one pot. The reactions occur under mild conditions with yields up to 90 %. A perfect regioselectivity is obtained, which can be rationalized through a mechanistic hypothesis that considers 1) the formation of an oxonium ylide, 2) its transformation into an unsaturated acyclic oxocarbenium electrophilic intermediate, and 3) an intramolecular nucleophilic attack in a direct application of Baldwin’s rules.
Keywords CarbenoidsDiazo compoundsMedium-ring compoundsRhodiumYlides
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Other version: http://doi.wiley.com/10.1002/chem.201103870
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BALLESTEROS GARRIDO, Rafael et al. Medium-Sized Rings versus Macrocycles through Rhodium-Catalyzed Ring-Expansion Reactions of Cyclic Acetals. In: Chemistry - A European Journal, 2012, vol. 18, n° 21, p. 6626-6631. https://archive-ouverte.unige.ch/unige:20422

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Deposited on : 2012-05-22

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