Merging Iron Catalysis and BiocatalysisIron Carbonyl Complexes as Efficient Hydrogen Autotransfer Catalysts in Dynamic Kinetic Resolutions

被引：68
作者：
El-Sepelgy, Osama [1 ]
Alandini, Nurtalya [1 ]
Rueping, Magnus [1 ,2 ]
机构：
[1] Rhein Westfal TH Aachen, Inst Organ Chem, Landoltweg 1, D-52074 Aachen, Germany
[2] KAUST, KAUST Catalysis Ctr KCC, Thuwal 239556900, Saudi Arabia
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 43期
关键词：
chiral alcohols; hydrogenases; kinetic resolution; lipases; reduction; OPPENAUER-TYPE OXIDATION; SECONDARY ALCOHOLS; ENZYMATIC RESOLUTION; REDUCTIVE AMINATION; ORGANIC-SYNTHESIS; ALLYLIC ALCOHOLS; ENANTIOSELECTIVE HYDROGENATION; CYCLOPENTADIENONE CATALYST; TRANSITION-METAL; AMINES;
D O I：
10.1002/anie.201606197
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A dual catalytic iron/lipase system has been developed and applied in the dynamic kinetic resolution of benzylic and aliphatic secondary alcohols. A detailed study of the Knolker-type iron complexes demonstrated the hydrogen autotransfer of alcohols to proceed under mild reaction conditions and allowed the combination with the enzymatic resolution. Different racemic alcohols were efficiently converted to chiral acetates in good yields and with excellent enantioselectivities.
引用
收藏
页码：13602 / 13605
页数：4
相关论文
共 75 条
[1]   Racemization catalysts for the dynamic kinetic resolution of alcohols and amines [J].
Ahn, Yangsoo ;
Ko, Soo-Byung ;
Kim, Mahn-Joo ;
Park, Jaiwook .
COORDINATION CHEMISTRY REVIEWS, 2008, 252 (5-7) :647-658
[2]   A dynamic kinetic esolution of allyl alcohols by the combined use of lipases and [VO(OSiPh3)3] [J].
Akai, S ;
Tanimoto, K ;
Kanao, Y ;
Egi, M ;
Yanamoto, T ;
Kita, Y .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (16) :2592-2595
[3]  
Akai S., 2006, ANGEW CHEM, V118, P2654
[4]  
[Anonymous], 2011, ANGEW CHEM, DOI [10.1002/ange.201004101, DOI 10.1002/ANGE.201004101]
[5]  
[Anonymous], 1999, ANGEW CHEM
[6]   Enantioselective Synthesis of Alcohols and Amines by Iridium-Catalyzed Hydrogenation, Transfer Hydrogenation, and Related Processes [J].
Bartoszewicz, Agnieszka ;
Ahlsten, Nanna ;
Martin-Matute, Belen .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (23) :7274-7302
[7]   Iron Catalysis in Organic Synthesis [J].
Bauer, Ingmar ;
Knoelker, Hans-Joachim .
CHEMICAL REVIEWS, 2015, 115 (09) :3170-3387
[8]  
Berkessel A., 2006, Angew. Chem, V118, P6717
[9]   Lipase/aluminum-catalyzed dynamic kinetic resolution of secondary alcohols [J].
Berkessel, Albrecht ;
Sebastian-Ibarz, M. Luisa ;
Mueller, Thomas N. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (39) :6567-6570
[10]   Light-Induced Enantioselective Hydrogenation Using Chiral Derivatives of Casey's Iron-Cyclopentadienone Catalyst [J].
Berkessel, Albrecht ;
Reichau, Sebastian ;
von der Hoeh, Adrian ;
Leconte, Nicolas ;
Neudoerfl, Joerg-M. .
ORGANOMETALLICS, 2011, 30 (14) :3880-3887
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