Use of a Semihollow-Shaped Triethynylphosphane Ligand for Efficient Formation of Six- and Seven-Membered Ring Ethers through Gold(I)-Catalyzed Cyclization of Hydroxy-Tethered Propargylic Esters

被引：19

作者：

Ito, Hideto ^{[1
]}

Harada, Ayumi ^{[1
]}

Ohmiya, Hirohisa ^{[1
]}

Sawamura, Masaya ^{[1
]}

机构：

[1] Hokkaido Univ, Fac Sci, Dept Chem, Sapporo, Hokkaido 0600810, Japan

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2013年 / 355卷 / 04期

关键词：

cyclization; gold; propargylic esters; seven-membered rings; triethnylphosphane; BULKY END CAPS; CATALYZED SYNTHESIS; GOLD; CONSTRUCTION; HETEROCYCLES; FRAMEWORKS; COMPLEX;

D O I：

10.1002/adsc.201200949

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The formation of six- and seven-membered ring ethers from hydroxy-tethered propargylic esters was efficiently catalyzed by a cationic gold(I) complex with a semihollow-shaped triethynylphosphane ligand. This gold catalysis showed a tolerance toward the reactions of primary, secondary, and tertiary alcohol substrates with various substitution patterns. A sterically congested 2,2,6,6-tetraalkyl-substituted tetrahydropyran derivative as well as 6,6- and 7,6-fused bicyclic diethers were obtained in useful yields. In addition, the gold catalysis was applicable to the reaction of a sulfonamide-tethered propargylic ester to give a piperidine derivative.

引用

页码：647 / 652

页数：6