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Synthesis of Substituted Tetralins and Benzosuberans via BF3·OEt2‑Mediated Formal (4 + 2) and (5 + 2) Stereocontrolled Cycloaddition of 4‑Alkenols with Veratrol

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posted on 04.02.2016, 16:22 authored by Meng-Yang Chang, Yu-Chieh Cheng
BF3·OEt2-mediated one-pot formal (4 + 2) and (5 + 2) stereocontrolled cycloaddition of 4-alkenols 3 and 4 with veratrol affords the respective substituted tetralins 5 and benzosuberans 6 in good yields. The cascade protocol combines a facile double Friedel–Crafts benzannulation of 4-alkenols 3 and 4 (having two electrophilic sites) and veratrol (7a) (having two nucleophilic sites). A plausible mechanism was studied and proposed.

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