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Communication | Special issue | Vol 77, No. 1, 2009, pp.201-206
Published online, 24th July, 2008
DOI: 10.3987/COM-08-S(F)25
An Efficient Synthetic Method for 3-Bromofuran Derivatives via Stereoselective Cyclization of γ,δ-Epoxy (E)-α-Bromoacrylates

Fumihiko Yoshimura, Masaki Takahashi, Keiji Tanino, and Masaaki Miyashita*

*Department of Applied Chemistry, Faculty of Engineering, Kogakuin University, 2665-1 Nakano-cho, Hachioji, Tokyo 192-0015, Japan

Abstract

A novel and efficient synthetic method for 3-bromofuran derivatives via stereoselective cyclization of γ,δ-epoxy-(E)-α-bromoacrylates is described. The reaction of a γ,δ-epoxy-(E)-α-bromoacrylate with MeAl3-H2O gave rise to a 3-bromo-2-methylfuran derivative, i.e., methylated bromofuran at the 2-position, while the reaction with Me3Al-(CF3)2CHOH reagent produced a 2-alkoxy-3-bromofuran derivative in high yield. The 3-bromofuran obtained was transformed into various functionalized furan derivatives.