Iridium-Catalyzed Asymmetric Hydrogenation of Substituted Pyridines

被引：23

作者：

Cadu, Alban ^{[2
]}

Upadhyay, Puspesh K. ^{[1
]}

Andersson, Pher G. ^{[1
,3
]}

机构：

[1] Stockholm Univ, Dept Organ Chem, Arrhenius Lab, SE-10691 Stockholm, Sweden

[2] Uppsala Univ, Dept Chem BMC, SE-75123 Uppsala, Sweden

[3] Univ KwaZulu Natal, Sch Chem & Phys, ZA-4000 Durban, South Africa

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2卷 / 12期

基金：

瑞典研究理事会;

关键词：

hydrogenation; iridium; N-iminopyridium ylides; pyridines; selective catalysis; ENANTIOSELECTIVE HYDROGENATION; OLEFINS; COMPLEXES; MECHANISM; LIGANDS; PIPERIDINE;

D O I：

10.1002/ajoc.201300160

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric hydrogenation of ortho-substituted pyridines catalyzed by N,P-ligated iridium is demonstrated. To facilitate this reaction, the aromaticity of the pyridines was weakened by forming N-iminopyridium ylides. The reactions give very high conversions, and after a single recrystallization, excellent ee of up to 98% was obtained. This method lends itself to the synthesis of chiral piperidine building blocks.

引用

页码：1061 / 1065

页数：5

共 65 条

[31] ASYMMETRIC HYDROGENATION OF METHYL-(Z)-ALPHA-ACETAMIDOCINNAMATE CATALYZED BY (1,2-BIS((PHENYL-ORTHO-ANISOYL)PHOSPHINO)ETHANE)RHODIUM(I) - KINETICS, MECHANISM, AND ORIGIN OF ENANTIOSELECTION [J].