Diethylaminosulfur Trifluoride (DAST)-Mediated Intramolecular Benzannulation of o-Allylchalcones: Synthesis of 3-Fluorotetralins

Meng-Yang Chang; Han-Yu Chen; Yu-Lin Tsai

doi:10.1055/s-0037-1612419

Synthesis, Inhaltsverzeichnis

Synthesis 2019; 51(12): 2553-2563
DOI: 10.1055/s-0037-1612419

paper

Diethylaminosulfur Trifluoride (DAST)-Mediated Intramolecular Benzannulation of o-Allylchalcones: Synthesis of 3-Fluorotetralins

Meng-Yang Chang *

^aDepartment of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan

^bDepartment of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung 807, Taiwan eMail: mychang@kmu.edu.tw

,

Han-Yu Chen

^aDepartment of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan

,

Yu-Lin Tsai

^aDepartment of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan

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Abstract

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Abstract

A concise route for the synthesis of 3-fluorotetralines is described, including: (i) NaBH₄-mediated reduction of oxygenated o-allylchalcones and (ii) sequential DAST-mediated intramolecular annulation of the resulting alkenols. A plausible mechanism is proposed and discussed. This protocol provides highly effective regio- and stereocontrolled allyl-enone cross-coupling to construct two stereocenters and one E-configured styryl group.

Key words

DAST - intramolecular benzannulation - o-allylchalcones - cross-coupling reaction - 3-fluorotetralines

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Referenzen

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