Enantioselective Hydrogenation of the Double Bond of Exocyclic α,β-Unsaturated Carbonyl Compounds Catalyzed by Iridium/H8-BINOL-Derived Phosphine-Oxazoline Complexes

被引：19

作者：

Li, Qing ^{[1
,2
]}

Wan, Pin ^{[1
]}

He, Yuwei ^{[1
]}

Zhou, Yougui ^{[1
]}

Li, Lanning ^{[1
]}

Chen, Bin ^{[1
]}

Duan, Kun ^{[1
]}

Cao, Rihui ^{[1
]}

Zhou, Zhongyuan ^{[3
]}

Qiu, Liqin ^{[1
,4
]}

机构：

[1] Sun Yat Sen Univ, Guangdong Engn Res Ctr Chiral Drugs, Sch Chem & Chem Engn, Guangzhou 510275, Guangdong, Peoples R China

[2] Guangzhou BaiYunShan Chem Pharmaceut Factory, Guangzhou 510515, Guangdong, Peoples R China

[3] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Hong Kong, Hong Kong, Peoples R China

[4] Sun Yat Sen Univ, Huizhou Res Inst, Dayawan, Huizhou, Peoples R China

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 3卷 / 07期

基金：

中国国家自然科学基金;

关键词：

asymmetric hydrogenation; iridium; oxazolines; phosphine ligands; alpha; beta-unsaturated carbonyl compounds; ASYMMETRIC HYDROGENATION; CARBOXYLIC-ACIDS; C=C BOND; KETONES; LIGANDS; ALDEHYDES; OLEFINS; IMINES; ALPHA; DERIVATIVES;

D O I：

10.1002/ajoc.201402011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

H-8-BINOL-derived phosphine-oxazolines complexed with iridium were successfully applied for the asymmetric hydrogenation of the carbon-carbon double bond of exocyclic alpha,beta-unsaturated carbonyl compounds. A valuable series of alpha-chiral cyclic ketones, lactones, and lactams were therefore provided via the reaction in high yields and good to excellent enantioselectivity of up to 95% ee. The effects of the ligands and substrate structures on the asymmetric catalysis were also discussed.

引用

页码：774 / 783

页数：10

共 69 条

[11] IRIDIUM COMPOUNDS IN CATALYSIS [J].