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Oxacycle Synthesis via Intramolecular Reaction of Carbanions and

By Rachel Will, Benjamin W. Puffer and Patrick H. Dussault


ABSTRACT: The intramolecular reaction of dialkyl peroxides with carbanions, generated via chemoselective metal-heteroatom exchange or deprotonation, provides a new approach to cyclic ethers. Applied in tandem with C− C bond formation, the strategy enables a one-step annelation to form oxaospirocycles. Ethers, which comprise critical substructures in manybioactive molecules and natural products,1 are typically synthesized through attack of nucleophilic oxygen on an electrophilic carbon.1,2 The converse of this strategy, attack of a carbanion on electrophilic oxygen, has been investigated to only a limited extent for intermolecular reactions and is essentially unexplored for intramolecular reactions. We now demonstrate that chemoselective generation of carbanions in the presence of appropriately positioned O−O bonds of dialkyl peroxides allows the efficient introduction of cyclic ethers (Figure 1)

Year: 2016
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