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

By Meng-Yang Chang (1393948) and Yu-Chieh Cheng (1393951)

Abstract

BF<sub>3</sub>·OEt<sub>2</sub>-mediated one-pot formal (4 + 2) and (5 + 2) stereocontrolled cycloaddition of 4-alkenols <b>3</b> and <b>4</b> with veratrol affords the respective substituted tetralins <b>5</b> and benzosuberans <b>6</b> in good yields. The cascade protocol combines a facile double Friedel–Crafts benzannulation of 4-alkenols <b>3</b> and <b>4</b> (having two electrophilic sites) and veratrol (<b>7a</b>) (having two nucleophilic sites). A plausible mechanism was studied and proposed

Topics: Biophysics, Biochemistry, Cell Biology, Molecular Biology, Ecology, Cancer, Computational Biology, Chemical Sciences not elsewhere classified, Physical Sciences not elsewhere classified, BF, alkenol, mechanism, tetralins 5, cycloaddition, nucleophilic sites, VeratrolBF, Stereocontrolled, benzannulation, Formal, Benzosuberan, stereocontrolled, Friedel, veratrol, Substituted Tetralins, Alkenol, cascade protocol, yield, electrophilic sites, benzosuberans 6, Synthesi, Cycloaddition
Year: 2016
DOI identifier: 10.1021/acs.orglett.5b03696.s013
OAI identifier: oai:figshare.com:article/2071645
Provided by: FigShare
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