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Synthesis of Substituted Tetralins and Benzosuberans via BF 3 ·OEt 2 -Mediated Formal (4 + 2) and (5 + 2) Stereocontrolled Cycloaddition of 4-Alkenols with Veratrol

2016; American Chemical Society; Volume: 18; Issue: 3 Linguagem: Inglês

10.1021/acs.orglett.5b03696

1523-7060

Meng‐Yang Chang, Yu‐Chieh Cheng,

Synthetic Organic Chemistry Methods

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.