Ruthenium-catalyzed cycloaddition between propargylic alcohols and cyclic 1,3-dicarbonyl compounds via an allenylidene intermediate

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

doi:10.1021/jo0357465

Ruthenium-catalyzed cycloaddition between propargylic alcohols and cyclic 1,3-dicarbonyl compounds via an allenylidene intermediate

J Org Chem. 2004 May 14;69(10):3408-12. doi: 10.1021/jo0357465.

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, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan. ynishiba@scl.kyoto-u.ac.jp

PMID: 15132549
DOI: 10.1021/jo0357465

Abstract

Thiolate-bridged diruthenium complexes such as [Cp*RuCl(mu(2)-SR)(2)RuCp*Cl] (Cp* = eta(5)-C(5)Me(5); R = Me, (n)Pr, (i)Pr) and [Cp*RuCl(mu(2)-S(i)Pr)(2)RuCp*(OH(2))]OTf (OTf = OSO(2)CF(3)) promote the cycloaddition between propargylic alcohols and cyclic 1,3-dicarbonyl compounds to give either the corresponding 4,6,7,8-tetrahydrochromen-5-ones or 4H-cyclopenta[b]pyran-5-ones in high yields with complete regioselectivity. This catalytic cycloaddition provides a simple and one-pot synthetic protocol for a variety of substituted chromenones and cyclopenta[b]pyranones.