Synlett 2010(19): 2843-2846  
DOI: 10.1055/s-0030-1259013
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (E)-1-Benzyloxy-3-fluoro-1,3-butadiene: A Novel Fluorinated Diene for Diels-Alder Reactions

Tsuyoshi Hayashi, Yoshinosuke Usuki*, Yosuke Wakamatsu, Hideo Iio
Department of Material Science, Graduate School of Science, Osaka City University, Sugimoto, Sumioshi-ku, Osaka 558-8585, Japan
Fax: +81(6)66052522; e-Mail: usuki@sci.osaka-cu.ac.jp.;
Further Information

Publication History

Received 1 September 2010
Publication Date:
22 October 2010 (online)

Abstract

A new approach has been developed for the synthesis of the fluorinated Kitahara-Danishefsky’s diene analogue, (E)-1-benzyloxy-3-fluoro-1,3-butadiene, via a Pd-catalyzed process. This novel fluorine-containing diene reacts with various dienophiles to provide useful 1-fluorocyclohexene derivatives in good yields.