Combined Ruthenium(II) and Lipase Catalysis for Efficient Dynamic Kinetic Resolution of Secondary Alcohols. Insight into the Racemization Mechanism

2005 ◽  
Vol 127 (24) ◽  
pp. 8817-8825 ◽  
Author(s):  
Belén Martín-Matute ◽  
Michaela Edin ◽  
Krisztián Bogár ◽  
F. Betül Kaynak ◽  
Jan-E. Bäckvall
Keyword(s):  
Kinetic Resolution ◽  
Secondary Alcohols ◽  
Dynamic Kinetic Resolution ◽  
Lipase Catalysis ◽  
Insight Into

scholarly journals Combined Ruthenium(II) and Lipase Catalysis for Efficient Dynamic Kinetic Resolution of Secondary Alcohols. Insight into the Racemization Mechanism.

ChemInform ◽  
2005 ◽  
Vol 36 (43) ◽  
Author(s):  
Belen Martin-Matute ◽  
Michaela Edin ◽  
Krisztian Bogar ◽  
Betuel Kaynak ◽  
Jan-E. Baeckvall
Keyword(s):  
Kinetic Resolution ◽  
Secondary Alcohols ◽  
Dynamic Kinetic Resolution ◽  
Lipase Catalysis ◽  
Insight Into

(S)-Selective Kinetic Resolution and Chemoenzymatic Dynamic Kinetic Resolution of Secondary Alcohols.

ChemInform ◽  
2006 ◽  
Vol 37 (16) ◽  
Author(s):  
Linnea Boren ◽  
Belen Martin-Matute ◽  
Yongmei Xu ◽  
Armando Cordova ◽  
Jan-E. Baeckvall
Keyword(s):  
Kinetic Resolution ◽  
Secondary Alcohols ◽  
Dynamic Kinetic Resolution

Efficient dynamic kinetic resolution of secondary alcohols with a novel tetrafluorosuccinato ruthenium complex

2006 ◽  
Vol 17 (15) ◽  
pp. 2299-2305 ◽  
Author(s):  
Sjoerd F.G.M. van Nispen ◽  
Jeroen van Buijtenen ◽  
Jef A.J.M. Vekemans ◽  
Jan Meuldijk ◽  
Lumbertus A. Hulshof
Keyword(s):  
Kinetic Resolution ◽  
Ruthenium Complex ◽  
Secondary Alcohols ◽  
Dynamic Kinetic Resolution

Lipase-mediated dynamic kinetic resolution (DKR) of secondary alcohols in the presence of zeolite using an ionic liquid solvent system

2015 ◽  
Vol 255 ◽  
pp. 41-48 ◽  
Author(s):  
Ken-ichi Shimomura ◽  
Hiroyuki Harami ◽  
Yui Matsubara ◽  
Toshiki Nokami ◽  
Naonobu Katada ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Kinetic Resolution ◽  
Solvent System ◽  
Secondary Alcohols ◽  
Dynamic Kinetic Resolution

Improved synthesis of Bn5CpRu(CO)2Cl and its application as racemization catalyst in preparative-scale metalloenzymatic dynamic kinetic resolution of 1-phenylethanol

2010 ◽  
Vol 83 (3) ◽  
pp. 479-487 ◽  
Author(s):  
Denys Mavrynsky ◽  
Liisa T. Kanerva ◽  
Reijo Sillanpää ◽  
Reko Leino
Keyword(s):  
Kinetic Resolution ◽  
Immobilized Enzyme ◽  
Metal Catalyst ◽  
Secondary Alcohols ◽  
Mass Loading ◽  
Dynamic Kinetic Resolution ◽  
Preparative Scale ◽  
Highly Active ◽  
Complex Forms

An improved gram-scale synthesis of Bn5CpRu(CO)2Cl is reported based on heating of pentabenzylcyclopentadiene with Ru3(CO)12 at 160 °C under argon atmosphere in mesitylene followed by addition of chloroform, continued heating, and evaporation of the solvents. Subsequent washing of unreacted ligand precursor with hexane provided pure title compound in 77 % yield. In combination with Candida antarctica lipase B (CAL-B) (Novozym 435), this complex forms a highly active racemization catalyst for metallo-enzymatic dynamic kinetic resolution (DKR) of secondary alcohols as demonstrated in the present work by converting 100 g of racemic 1-phenylethanol to (R)-1-phenylethanol in >99 % ee and 93 % overall yield over two steps using 0.05 mol % loading of the metal catalyst and 1 mass % loading of immobilized enzyme. In addition, the synthesis and crystallographic characterization of the palladium congener Bn5CpPd(PPh3)Cl are briefly discussed.

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