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Cycloisomerization Promoted by the Combination of a Ruthenium-Carbene Catalyst and Trimethylsilyl Vinyl Ether, and its Application in The Synthesis of Heterocyclic Compounds: 3-Methylene-2,3-dihydroindoles and 3-Methylene-2,3-dihydrobenzofurans

Yukiyoshi Terada, Mitsuhiro Arisawa, Atsushi Nishida*

*Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan, Email: nishidap.chiba-u.ac.jp

Y. Terada, M. Arisawa, A. Nishida, Angew. Chem. Int. Ed., 2004, 43, 4063-4067.

DOI: 10.1002/anie.200454157 (free Supporting Information)


Abstract

A new methodology for the cycloisomerization of dienes using a Grubbs carbene complex and trimethylsilyl vinyl ether has been established. The utility of this reaction was demonstrated by in the synthesis of exo-methylene heterocyclic compounds, which could act as key intermediates for pharmacologically active compounds.

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Key Words

cyclization, heterocycles, pyrrolidines, cyclopentanes, tetrahedrofurans, isomerization, metathesis, ruthenium


ID: J06-Y2004-510