Rapid atropisomerization of 1,1′:5′,1″-ternaphthalene-2,2′,6′,2″-tetrol (TERNOL) and its inhibition by tethering at positions 7 and 7″ |
| |
Authors: | Takashi Sugimura Naohiro Matsushita Keiko Minokami Shinya Kurita |
| |
Institution: | Graduate School of Material Science, Himeji Institute of Technology, University of Hyogo, 3-2-1 Kohto, Kamigori, Ako-gun, Hyogo 678-1297, Japan |
| |
Abstract: | Atropisomerization of 1,1′:5′,1″-ternaphthalene-2,2′,6′,2″-tetrol (TERNOL) is very fast under basic conditions. The stereochemical instability is attributed to the nature of oxide anion of the central 2,6-naphthodiol moiety. Ring-closing metathesis of 7,7″-diallyloxy TERNOL results in intramolecular tethering in a high yield, which intrinsically inhibits the rapid isomerization. Bidentate sites in the tethered TERNOL are proved to have enough structural flexibility as an axial chiral ligand. |
| |
Keywords: | Axial chirality Atropisomerization Bidentate ligand Metathesis |
本文献已被 ScienceDirect 等数据库收录! |
|