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Two concise methods for generating oxetan-3-ones from allenes are reported. The first method employs allene epoxidation, opening of the spirodiepoxide by a halide nucleophile, and then intramolecular displacement of a halide by an alkoxide. The second method involves allene epoxidation and then thermal rearrangement of the corresponding spirodiepoxide to oxetan-3-one. The two methods are complementary and stereochemically divergent. Computational analysis of the thermal rearrangement is also described.


Rojita Sharma, Lawrence J Williams. Oxetan-3-ones from allenes via spirodiepoxides. Organic letters. 2013 May 3;15(9):2202-5

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PMID: 23617820

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