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20.6.1.3.3 Variation 3: δ-Lactones from the Opening of Epoxides with C3 Building Blocks

DOI: 10.1055/sos-SD-020-01369

Maier, M. E.Science of Synthesis, (2007201451.

The use of C3 nucleophiles that carry a carboxy function or an equivalent thereof in the reaction with epoxides can lead to δ-lactones. One useful reagent in this regard is trimethyl 3-(phenylsulfonyl)orthopropanoate (55), which serves as a practical homoenolate reagent (Scheme 47).[‌121‌] Deprotonation next to the sulfonyl group at 78°C, followed by addition of an epoxide at 20°C and acidic workup, causes lactonization to the δ-lactones 110.[‌122‌] Upon treatment with base the unsaturated lactones 111 are obtained. The yields are good for monosubstituted epoxides.

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References


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