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

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

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...

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Veröffentlicht in:Organic letters 2016-02, Vol.18 (3), p.608-611
Hauptverfasser: Chang, Meng-Yang, Cheng, Yu-Chieh
Format: Artikel
Sprache:eng
Schlagworte:
Alcohols - chemical synthesis
Alcohols - chemistry
Anisoles - chemical synthesis
Anisoles - chemistry
Catalysis
Crystallography, X-Ray
Cyclization
Cycloaddition Reaction
Molecular Conformation
Molecular Structure
Stereoisomerism
Tetrahydronaphthalenes - chemical synthesis
Tetrahydronaphthalenes - chemistry
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b03696