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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

Author:
Chang, Meng-Yang, Cheng, Yu-Chieh
Source:
Organic letters 2016 v.18 no.3 pp. 608-611
ISSN:
1523-7052
Subject:
Lewis acids, Lewis bases, chemical structure, cycloaddition reactions, organic compounds
Abstract:
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.
Agid:
5792324