Enantioselective Hydrogenation of Ketones using Different Metal Complexes with a Chiral PNP Pincer Ligand

被引：41
|
作者：
Garbe, Marcel [1 ]
Wei, Zhihong [1 ]
Tannert, Bianca [1 ]
Spannenberg, Anke [1 ]
Jiao, Haijun [1 ]
Bachmann, Stephan [2 ]
Scalone, Michelangelo [2 ]
Junge, Kathrin [1 ]
Beller, Matthias [1 ]
机构：
[1] Univ Rostock, Leibniz Inst Katalyse eV, Albert Einstein Str 29a, D-18059 Rostock, Germany
[2] F Hoffmann La Roche Ltd, Proc Chem & Catalysis, Grenzacherstr 124, CH-4070 Basel, Switzerland
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2019年 / 361卷 / 08期
关键词：
Asymmetric Catalysis; Chiral Pincer; Asymmetric Hydrogenation; Prochiral Ketones; Chiral Alcohols; CATALYTIC ASYMMETRIC HYDROGENATION; P-N-P'; IRON(II) COMPLEXES; COBALT COMPLEXES; WELL;
D O I：
10.1002/adsc.201801511
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
The synthesis of different metal pincer complexes coordinating to the chiral PNP ligand bis(2-((2R,5R)-2,5-dimethyl-phospholanoethyl))amine is described in detail. The characterized complexes with Mn, Fe, Re and Ru as metal centers showed good activities regarding the reduction of several prochiral ketones. Comparing these catalysts, the non-noble metal complexes produced best selectivities not only for aromatic substrates, but also for different kinds of aliphatic ones leading to enantioselectivities up to 99% ee. Theoretical investigations elucidated the mechanism and rationalized the selectivity.
引用
收藏
页码：1913 / 1920
页数：8
相关论文
共 50 条
  • [41] Metal-Ligand Cooperation Facilitates Bond Activation and Catalytic Hydrogenation with Zinc Pincer Complexes
    Rauch, Michael
    Kar, Sayan
    Kumar, Amit
    Avram, Liat
    Shimon, Linda J. W.
    Milstein, David
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (34) : 14513 - 14521
  • [42] Rhodium(III) NCN pincer complexes catalyzed transfer hydrogenation of ketones
    Raja, Mathiyazhagan Ulaganatha
    Ramesh, Rengan
    Ahn, Kyo Han
    TETRAHEDRON LETTERS, 2009, 50 (50) : 7014 - 7017
  • [43] Highly enantioselective transfer hydrogenation of aromatic ketones catalyzed by chiral diaminodiphosphine-iridium(I) complexes
    Tang, CL
    Li, YY
    Pan, ED
    Zhang, H
    Zhou, ZH
    Gao, JX
    ACTA CHIMICA SINICA, 2001, 59 (10) : 1831 - 1834
  • [44] Molecularly Defined Manganese Pincer Complexes for Selective Transfer Hydrogenation of Ketones
    Perez, Marc
    Elangovan, Saravanakumar
    Spannenberg, Anke
    Junge, Kathrin
    Beller, Matthias
    CHEMSUSCHEM, 2017, 10 (01) : 83 - 86
  • [45] Asymmetric transfer hydrogenation of ketones catalyzed by ruthenium(II) complexes bearing a chiral phosphinoferrocenyloxazoline ligand
    Madrigal, Cesar A.
    Garcia-Fernandez, Almudena
    Gimeno, Jose
    Lastra, Elena
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2008, 693 (15) : 2535 - 2540
  • [46] Pd(II)-NNN Pincer Complexes for Catalyzing Transfer Hydrogenation of Ketones
    Jerome, Peter
    Haribabu, Jebiti
    Bhuvanesh, Nattamai S. P.
    Karvembu, Ramasamy
    CHEMISTRYSELECT, 2020, 5 (43): : 13591 - 13597
  • [47] Highly enantioselective hydrogenation catalyzed by transition metal complexes with new chiral phosphines.
    Zhang, XM
    Zhang, ZG
    Zhu, GX
    Jiang, QZ
    Xiao, DM
    Cao, P
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 216 : U34 - U34
  • [48] Highly enantioselective hydrogenation catalyzed by transition metal complexes with new chiral phosphines.
    Zhang, XM
    Cao, P
    Chen, AG
    Jiang, QZ
    Xiao, DM
    Zhang, ZG
    Zhu, GX
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 217 : U174 - U174
  • [49] A new NCN pincer ruthenium complex and its catalytic activity for enantioselective hydrogenation of ketones
    Ito, Jun-Ichi
    Ujiie, Satoshi
    Nishiyama, Hisao
    CHEMICAL COMMUNICATIONS, 2008, (16) : 1923 - 1925
  • [50] Synthesis and reactivity of BINEPINE-based chiral Fe(II) PNP pincer complexes
    Christian Schröder-Holzhacker
    Nikolaus Gorgas
    Berthold Stöger
    Karl Kirchner
    Monatshefte für Chemie - Chemical Monthly, 2016, 147 : 1023 - 1030
12345