Development of an Efficient Stereoretentive Para ‐Claisen‐Cope Rearrangement

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A stereoretentive para ‐Claisen‐Cope rearrangement of chiral aryl‐allyl ethers is reported, achieving near‐perfect chirality transfer thereby furnishing products with exceptional enantiomeric excess (up to > 98% ee ) as single regioisomers. This transformation is operationally simple, air‐ and moisture‐tolerant, and catalyzed by a commercially available Europium (III) complex. Mechanistic studies suggest that this para ‐Claisen‐Cope process involves two consecutive [3,3]‐sigmatropic rearrangements, resulting in overall retention of stereochemistry. Furthermore, an optimized asymmetric allylic alkylation protocol enables the straightforward preparation of enantioenriched aryl‐allyl ether substrates with high enantiomeric purity. Both transformations exhibit broad functional group tolerance, affording the desired products in good to excellent yields.

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