Ir-catalyzed asymmetric hydrogenation of β-keto esters with chiral ferrocenyl P, N, N-ligands

被引：18

作者：

Chen, Xiu-Shuai ^{[1
,2
]}

Hou, Chuan-Jin ^{[1
,3
]}

Qin, Chao ^{[1
,2
]}

Liu, Hongzhu ^{[3
]}

Liu, Yan-Jun ^{[1
]}

Huang, De-Zhi ^{[1
]}

Hu, Xiang-Ping ^{[2
]}

机构：

[1] Dalian Polytech Univ, Sch Light Ind & Chem Engn, Dalian 116034, Peoples R China

[2] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China

[3] Dalian Zhenbang Fluorocarbon Paint Stock Co Ltd, Postdoctoral Res Stn, Dalian 116036, Peoples R China

来源：

RSC ADVANCES | 2017年 / 7卷 / 21期

基金：

中国国家自然科学基金;

关键词：

FORMAL 3+2 CYCLOADDITION; DECARBOXYLATIVE PROPARGYLIC ALKYLATION; ENANTIOSELECTIVE HYDROGENATION; DIPHOSPHINE LIGANDS; HIGHLY EFFICIENT; DIPYRIDYLPHOSPHINE LIGAND; ALLYLIC SUBSTITUTION; KINETIC RESOLUTION; IRIDIUM CATALYSTS; KETOESTERS;

D O I：

10.1039/c7ra00472a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The Ir-catalyzed asymmetric hydrogenation of beta-keto esters with chiral ferrocenyl P, N, N-ligands has been developed. Under the optimized conditions, a wide range of beta-keto esters were hydrogenated to afford the corresponding beta-hydroxy esters in good to excellent enantioselectivities (up to 95% ee).

引用

页码：12871 / 12875

页数：5

共 59 条

[1]

Andrushko V., 2013, STEREOSELECTIVE SYNT, P909

[2]

[Anonymous], 2007, The Handbook of Homogeneous Hydrogenation

[3] Development of Chiral Spiro P-N-S Ligands for Iridium-Catalyzed Asymmetric Hydrogenation of -Alkyl--Ketoesters [J].

Bao, Deng-Hui ;

Wu, Hui-Ling ;

Liu, Chao-Lun ;

Xie, Jian-Hua ;

Zhou, Qi-Lin .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (30) :8791-8794

[4] Studies on the chemoenzymatic synthesis of (R)- and (S)-methyl 3-aryl-3-hydroxypropionates: the influence of toluene-pretreatment of lipase preparations on enantioselective transesterifications [J].

Borowiecki, Pawel ;

Bretner, Maria .

TETRAHEDRON-ASYMMETRY, 2013, 24 (15-16) :925-936

[5] Enantioselective synthesis of chiral phosphonylated 2,3-dihydrofurans by copper catalyzed asymmetric formal [3+2] cycloaddition of propargylic esters with β-keto phosphonates [J].

Chen, Xiushuai ;

Hou, Chuanjin ;

Li, Qing ;

Liu, Yanjun ;

Yang, Ruifeng ;

Hu, Xiangping .

CHINESE JOURNAL OF CATALYSIS, 2016, 37 (08) :1389-1395

[6] Synthesis and molecular modeling studies of SYNPHOS®, a new, efficient diphosphane ligand for ruthenium-catalyzed asymmetric hydrogenation [J].

de Paule, SD ;

Jeulin, S ;

Ratovelomanana-Vidal, V ;

Genêt, JP ;

Champion, N ;

Dellis, P .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (10) :1931-1941

[7] ClickFerrophos: New chiral ferrocenyl phosphine ligands synthesized by Click Chemistry and the use of their metal complexes as catalysts for asymmetric hydrogenation and allylic substitution [J].

Fukuzawa, Shin-ichi ;

Oki, Hiroshi ;

Hosaka, Mitsuteru ;

Sugasawa, Jun ;

Kikuchi, Satoshi .

ORGANIC LETTERS, 2007, 9 (26) :5557-5560

[8] Highly Enantioselective Copper-Catalyzed Propargylic Substitution of Propargylic Acetates with 1,3-Dicarbonyl Compounds [J].

Han, Fu-Zhong ;

Zhu, Fu-Lin ;

Wang, Ya-Hui ;

Zou, Yuan ;

Hu, Xin-Hu ;

Chen, Song ;

Hu, Xiang-Ping .

ORGANIC LETTERS, 2014, 16 (02) :588-591

[9] Sterically Hindered Chiral Ferrocenyl P,N,N-Ligands for Highly Diastereo-/Enantioselective Ir-Catalyzed Hydrogenation of α-Alkyl-β-ketoesters via Dynamic Kinetic Resolution [J].

Hou, Chuan-Jin ;

Hu, Xiang-Ping .

ORGANIC LETTERS, 2016, 18 (21) :5592-5595

[10] Chiral, porous, hybrid solids for highly enantioselective heterogeneous asymmetric hydrogenation of β-keto esters [J].

Hu, A ;

Ngo, HL ;

Lin, WB .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (48) :6000-6003

← 1 2 3 4 5 6 →