Catalytic Asymmetric Hydrogenation of Pyrimidines

被引：48

作者：

Kuwano, Ryoichi ^{[1
,2
,3
]}

Hashiguchi, Yuta ^{[1
,2
]}

Ikeda, Ryuhei ^{[1
,2
]}

Ishizuka, Kentaro ^{[1
,2
,4
]}

机构：

[1] Kyushu Univ, Grad Sch Sci, Dept Chem, Higashi Ku, Fukuoka 8128581, Japan

[2] Kyushu Univ, IRCMS, Higashi Ku, Fukuoka 8128581, Japan

[3] JST ACT C, Higashi Ku, Fukuoka 8128581, Japan

[4] Kyushu Univ, Educ Ctr Global Leaders Mol Syst Devices, Nishi Ku, Fukuoka 8190395, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 08期

关键词：

asymmetric catalysis; heterocycles; hydrogenation; iridium; lanthanides; HIGHLY ENANTIOSELECTIVE HYDROGENATION; CHIRAL IRIDIUM COMPLEXES; HETEROAROMATIC-COMPOUNDS; PYRIDINIUM SALTS; ISOQUINOLINIUM SALTS; EFFICIENT ROUTE; QUINOXALINES; DERIVATIVES; QUINOLINES; INDOLES;

D O I：

10.1002/anie.201410607

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The asymmetric hydrogenation of pyrimidines proceeded with high enantioselectivity (up to 99%ee) using an iridium catalyst composed of [IrCl(cod)](2), a ferrocene-containing chiral diphosphine ligand (Josiphos), iodine, and Yb(OTf)(3) (cod=1,5-cyclooctadiene). The chiral catalyst converted various 4-substituted pyrimidines into chiral 1,4,5,6-tetrahydropyrimidines in high yield. The lanthanide triflate is crucial for achieving the high enantioselectivity as well as for activating the heteroarene substrate.

引用

页码：2393 / 2396

页数：4