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

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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