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DOI: 10.1055/sos-SD-031-00288

González-Bello, C.; Castedo, L.Science of Synthesis, (200731319.

The [3,3]-sigmatropic rearrangement of allyl aryl ethers, known as the aromatic Claisen rearrangement,[‌1‌‌3‌] affords allylphenols. 2-Allylphenols are usually the main product, but the para-Claisen rearrangement can compete. The original aromatic Claisen rearrangement conditions consist of heating at 150220°C. However, much milder reaction conditions have been developed that use microwave irradiation,[‌4‌] Lewis acids such as boron trichloride, boron trifluoridediethyl ether complex, diethylaluminum chloride, titanium(IV) chloride, and diisopropylaluminum chloride, or diverse catalysts such as zeolites.[‌5‌] For example, the Lewis acid catalyzed Claisen rearrangement of allyl ethers 1 and 3 affords phenols 2 and 4, respectively, in excellent yields (Scheme 1).[‌6‌,‌7‌]

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e M8 M8 M8 M8 ee (%) Meeee (%) Mee
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Meeeeeeeeee 8

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β-eeeeeeeeeeee (8 eeeee) M8M 88:88:8 [‌88‌,‌88‌]
β-eeeeeeeeeeee (88 eeeee) M8M 88:88:8 [‌88‌,‌88‌]
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Meeeeeeeeeee Meeeeeeee

8-Meeee-8-eeeeeeeeeee (8); Meeeeee Meeeeeeee:[‌8‌]

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