Gold-Catalyzed Cyclization of Alkyne Alcohols: Regioselective Construction of Functionalized 6,6- and 6,7-Bicyclic Ethers

Mio Kubota; Tatsuo Saito; Kazunori Miyamoto; Keiichi Hirano; Chao Wang; Masanobu Uchiyama

doi:10.1248/cpb.c16-00204

Special Collection of Papers: Regular Articles

Gold-Catalyzed Cyclization of Alkyne Alcohols: Regioselective Construction of Functionalized 6,6- and 6,7-Bicyclic Ethers

Mio Kubota, Tatsuo Saito, Kazunori Miyamoto, Keiichi Hirano, Chao Wang, Masanobu Uchiyama

Author information

Keywords: gold-catalysis, cyclization, hydroalkoxylation, polyether, tandem reaction

JOURNAL FREE ACCESS FULL-TEXT HTML

2016 Volume 64 Issue 7 Pages 845-855

DOI https://doi.org/10.1248/cpb.c16-00204

Details

Abstract

We describe an efficient regioselective formation of six-/seven-membered cyclic ethers based on gold-catalyzed intramolecular hydroalkoxylation. Sequential gold-catalyzed cyclization and palladium-catalyzed cross-coupling reactions afforded 6,6-bicyclic ethers, while reversing the reaction sequence (cross-coupling then cyclization) afforded 6,7-bicyclic ethers. This methodology should provide access to a range of functional polycyclic ethers.

Graphical Abstract Fullsize Image

Corresponding author

Register with J-STAGE for free!