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We report a catalytic C–O coupling/Claisen cascade reaction enabled by interception of vinyl carbocations with allyl ethers. The reaction utilizes commercially available borate salts as catalysts and is effective at constructing sterically hindered C–C bonds. The reaction mechanism is studied experimentally and computationally to support a charge-accelerated 3,3 rearrangement of a silyloxonium cation. Our reaction is also applied to the highly stereoselective synthesis of fully substituted vinyl ethers.
Williams et al. (Thu,) studied this question.