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Efficient generation of an oxidopyrylium ylide using a Pd catalyst and its [5+2] cycloadditions with several
Hiroyuki Suga1, Taichi Iwai, Masahiro Shimizu
1Department of Materials Chemistry, Faculty of Engineering, Shinshu University, Wakasato, Nagano 380-8553, Japan. sugahio@shinshu-u.ac.jp.
Abstract:
An efficient method for the generation of an oxidopyrylium ylide from 6-acetoxy-6-acetoxymethyl-2H-pyran-3(6H)-one using a Pd catalyst and [5+2] cycloadditions of the resulting ylide are described. Among substituted styrene derivatives as dipolarophiles, electron-rich styrenes showed higher yield (up to 80%). The [5+2] cycloaddition reactions can also be applied to exo-methylene cyclic compounds, and an improved method for the synthesis of polygalolide intermediate has been demonstrated.
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