An Efficient Synthesis of Chiral Alcohols via Catalytic Hydrogenation of Esters

被引：27

作者：

Ino, Yasunori ^{[1
]}

Kuriyama, Wataru ^{[1
]}

Ogata, Osamu ^{[1
]}

Matsumoto, Takaji ^{[1
]}

机构：

[1] Takasago Int Corp, Corp Res & Dev Div, Hiratsuka, Kanagawa 2540073, Japan

来源：

TOPICS IN CATALYSIS | 2010年 / 53卷 / 15-18期

关键词：

Ester; Hydrogenation; Homogeneous; Ruthenium; Catalyst; Chiral; Alcohol; Amino alcohol; Diol; ASYMMETRIC HYDROGENATION; STEREOSELECTIVE HYDROGENATION; KETONE HYDROGENATION; COMPLEXES; MECHANISM; LIGANDS;

D O I：

10.1007/s11244-010-9573-x

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A ruthenium complex was found to catalyze the hydrogenation of chiral esters without the loss of their optical purities under mild and neutral conditions. This method can avoid a violent quench step and an extraction step which accompany conventional reduction using metal hydride reagents such as sodium borohydride and lithium aluminum hydride.

引用

页码：1019 / 1024

页数：6

共 26 条

[1] Mechanism of the hydrogenation of ketones catalyzed by trans-dihydrido(diamine)ruthenium(II) complexes
Abdur-Rashid, K
Clapham, SE
Hadzovic, A
Harvey, JN
Lough, AJ
Morris, RH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (50) : 15104 - 15118
[2] BERTSCHY H, 1995, ENZYME CATALYSIS ORG, V2, P2227
[3] Doucet H, 1998, ANGEW CHEM INT EDIT, V37, P1703, DOI 10.1002/(SICI)1521-3773(19980703)37:12<1703::AID-ANIE1703>3.0.CO
[4] 2-I
[5] Asymmetric synthesis of active pharmaceutical ingredients
Farina, Vittorio
Reeves, Jonathan T.
Senanayake, Chris H.
Song, Jinhua J.
[J]. CHEMICAL REVIEWS, 2006, 106 (07) : 2734 - 2793
[6] Applications of ruthenium hydride borohydride complexes containing phosphinite and diamine ligands to asymmetric catalytic reactions
Guo, RW
Chen, XH
Elpelt, C
Song, DT
Morris, RH
[J]. ORGANIC LETTERS, 2005, 7 (09) : 1757 - 1759
[7] A mechanism displaying autocatalysis:: The hydrogenation of acetophenone catalyzed by RuH(S-binap)(app) where app is the amido ligand derived from 2-amino-2-(2-pyridyl)propane
Hadzovic, Alen
Song, Datong
MacLaughlin, Christina M.
Morris, Robert H.
[J]. ORGANOMETALLICS, 2007, 26 (24) : 5987 - 5999
[8] A ruthenium-dihydrogen putative intermediate in ketone hydrogenation
Hamilton, RJ
Leong, CG
Bigam, G
Miskolzie, M
Bergens, SH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (12) : 4152 - 4153
[9] Direct observations of the metal-ligand bifunctional addition step in an enantioselective ketone hydrogenation
Hamilton, Robin J.
Bergens, Steven H.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (36) : 11979 - 11987
[10] Supported organometallic complexes - Part XXXV. Synthesis, characterization, and catalytic application of a new family of diamine(diphosphine)ruthenium(II) complexes
Lindner, E
Mayer, HA
Warad, I
Eichele, K
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 665 (1-2) : 176 - 185

← 1 2 3 →