Ruthenium- and platinum-catalyzed sequential reactions: selective synthesis of fused polycyclic compounds from propargylic alcohols and alkenes

Yoshiaki Nishibayashi; Masato Yoshikawa; Youichi Inada; Masanobu Hidai; Sakae Uemura

doi:10.1021/ja045532k

Ruthenium- and platinum-catalyzed sequential reactions: selective synthesis of fused polycyclic compounds from propargylic alcohols and alkenes

J Am Chem Soc. 2004 Dec 15;126(49):16066-72. doi: 10.1021/ja045532k.

Authors

Yoshiaki Nishibayashi¹, Masato Yoshikawa, Youichi Inada, Masanobu Hidai, Sakae Uemura

Affiliation

¹ Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan. ynishiba@scl.kyoto-u.ac.jp

PMID: 15584741
DOI: 10.1021/ja045532k

Abstract

A simple method for the preparation of fused polycyclic compounds by an intramolecular cyclization of propargylic alcohols bearing an alkene moiety at a suitable position has been developed, where the presence of both Ru and Pt catalysts promotes a sequence of catalytic cycles in the same medium. This sequential system can be applied to an intermolecular reaction between a propargylic alcohol and an alkene to obtain the corresponding bicyclo[3,1,0]hex-2-ene derivative. These sequential reactions provide a conceptually new type of cycloaddition system between propargylic alcohols and alkenes.