Oxetan-3-ones from Allenes via Spirodiepoxides

Oxetan-3-ones from Allenes via Spirodiepoxides

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 ther...

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Veröffentlicht in:Organic letters 2013-05, Vol.15 (9), p.2202-2205
Hauptverfasser: Sharma, Rojita, Williams, Lawrence J
Format: Artikel
Sprache:eng
Schlagworte:
Alkadienes - chemistry
Ethers, Cyclic - chemistry
Molecular Structure
Spiro Compounds - chemistry
Stereoisomerism
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol400749e