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

Meng-Yang Chang (1393948); Yu-Chieh Cheng (1393951)

doi:10.1021/acs.orglett.5b03696.s002

Synthesis of Substituted Tetralins and Benzosuberans via BF3·OEt2‑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

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

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.s002

OAI identifier: oai:figshare.com:article/2071675

Provided by: FigShare

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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

Abstract

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