Ruthenium-catalyzed enantioselective reduction of electron-rich aryl alkyl ketones

被引：38

作者：

Wettergren, Jenny ^{[1
]}

Bogevig, Anders ^{[1
]}

Portier, Maud ^{[1
]}

Adolfsson, Hans ^{[1
]}

机构：

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

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2006年 / 348卷 / 10-11期

关键词：

asymmetric catalysis; hydrogen transfer; ketones; reduction; ruthenium;

D O I：

10.1002/adsc.200606067

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Presented here is the investigation of the transfer hydrogenation of electron-rich aryl alkyl ketones using ruthenium complexes of dipeptide-like ligands and 2-propanol as hydride source. The reduction proceeded with excellent selectivity (up to > 99 % ee) and in moderate to high yields (up to 90%).

引用

页码：1277 / 1282

页数：6

共 50 条

[1] Ruthenium-Catalyzed Enantioselective Hydrogenation of Aryl-Pyridyl Ketones
Tao, Xiaoming
Li, Wanfang
Ma, Xin
Li, Xiaoming
Fan, Weizheng
Xie, Xiaomin
Ayad, Tahar
Ratovelomanana-Vidal, Virginie
Zhang, Zhaoguo
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (01): : 612 - 616
[2] In situ formation of ligand and catalyst -: application in ruthenium-catalyzed enantioselective reduction of ketones
Västilä, P
Wettergren, J
Adolfsson, H
CHEMICAL COMMUNICATIONS, 2005, (32) : 4039 - 4041
[3] Highly enantioselective ruthenium-catalyzed reduction of ketones employing readily available peptide ligands
Bogevig, A
Pastor, IM
Adolfsson, H
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (01) : 294 - 302
[4] Direct Asymmetric Ruthenium-Catalyzed Reductive Amination of Alkyl-Aryl Ketones with Ammonia and Hydrogen
Gallardo-Donaire, Joan
Hermsen, Marko
Wysocki, Jedrzej
Ernst, Martin
Rominger, Frank
Trapp, Oliver
Hashmi, A. Stephen K.
Schaefer, Ansgar
Comba, Peter
Schaub, Thomas
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (01) : 355 - 361
[5] Benzimidazoles as Ligands in the Ruthenium-Catalyzed Enantioselective Bifunctional Hydrogenation of Ketones
Praetorius, Jeremy M.
Wang, Ruiyao
Crudden, Cathleen M.
ORGANOMETALLICS, 2010, 29 (03) : 554 - 561
[6] (Cyclopentadienyl)ruthenium-Catalyzed Regio- and Enantioselective Decarboxylative Allylic Etherification of Allyl Aryl and Alkyl Carbonates
Austeri, Martina
Linder, David
Lacour, Jerome
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (18) : 3339 - 3347
[7] Hydrosilanes are not always a reducing reagent: a ruthenium-catalyzed introduction of primary alkyl groups to electron-rich aromatic rings using esters as a source of the alkyl groups
Nagashima, Hideo
Kubo, Yuichi
Kawamura, Mitsunobu
Nishikata, Takashi
Motoyama, Yukihiro
TETRAHEDRON, 2011, 67 (40) : 7667 - 7672
[8] Enantioselective and regioselective ruthenium-catalyzed decarboxylative etherification of allyl aryl carbonates
Austeri, Martina
Linder, David
Lacour, Jerome
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (19) : 5737 - 5741
[9] Ni-Catalyzed Reductive Coupling of Electron-Rich Aryl Iodides with Tertiary Alkyl Halides
Wang, Xuan
Ma, Guobin
Peng, Yu
Pitsch, Chloe E.
Moll, Brenda J.
Ly, Thu D.
Wang, Xiaotai
Gong, Hegui
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (43) : 14490 - 14497
[10] New paracyclophane phosphine for highly enantioselective ruthenium-catalyzed hydrogenation of prochiral ketones
Cheemala, Murthy N.
Gayral, Maud
Brown, John M.
Rossen, Kai
Knochel, Paul
SYNTHESIS-STUTTGART, 2007, (24): : 3877 - 3885

← 1 2 3 4 5 →