1,2]- or [2,3]-rearrangement of onium ylides of allyl and benzyl ethers and sulfides via in situ-generated iodonium ylides |
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Authors: | Murphy Graham K West F G |
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Institution: | Department of Chemistry, University of Alberta, Edmonton, AB, Canada T6G 2G2. |
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Abstract: | Iodonium ylides, generated in situ with bisacetoxyiodobenzene, are converted to allyl- or benzyl-substituted oxonium or sulfonium ylides via rhodium- or copper-catalyzed carbene transfer. Except for the S-benzyl example, the resulting ylides undergo rearrangement to the corresponding 2-substituted heterocycles. This demonstrates the first use of iodonium ylides as diazoketone surrogates for the generation and rearrangement of onium ylide intermediates. This abbreviated one-step method proceeds in comparable yields relative to the corresponding two-step route employing diazoketone intermediates. |
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