scholarly journals Nonenzymatic Dynamic Kinetic Resolution of Secondary Alcohols via Enantioselective Acylation: Synthetic and Mechanistic Studies

2012 ◽  
Vol 134 (36) ◽  
pp. 15149-15153 ◽  
Author(s):  
Sarah Yunmi Lee ◽  
Jaclyn M. Murphy ◽  
Atsushi Ukai ◽  
Gregory C. Fu
Keyword(s):  
Kinetic Resolution ◽  
Secondary Alcohols ◽  
Mechanistic Studies ◽  
Dynamic Kinetic Resolution ◽  
Enantioselective Acylation

(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.

Core-Shell Composite as the Racemization Catalyst in the Dynamic Kinetic Resolution of Secondary Alcohols

ChemCatChem ◽  
2012 ◽  
Vol 5 (1) ◽  
pp. 247-254 ◽  
Author(s):  
Jie Wang ◽  
Dong-Minh Do ◽  
Gaik-Khuan Chuah ◽  
Stephan Jaenicke
Keyword(s):  
Kinetic Resolution ◽  
Core Shell ◽  
Secondary Alcohols ◽  
Dynamic Kinetic Resolution ◽  
Shell Composite

scholarly journals The Silicon–Hydrogen Exchange Reaction: Catalytic Kinetic Resolution of 2-Substituted Cyclic Ketones

Synlett ◽  
2021 ◽  
Author(s):  
Benjamin List ◽  
Hui Zhou ◽  
Pinglu Zhang
Keyword(s):  
Exchange Reaction ◽  
Hydrogen Exchange ◽  
Kinetic Resolution ◽  
Mechanistic Studies ◽  
Dynamic Kinetic Resolution ◽  
Cyclic Ketones ◽  
Silicon Source ◽  
Acid Catalyzed

We have recently reported the strong and confined, chiral acid-catalyzed asymmetric “silicon−hydrogen exchange reaction”. One aspect of this transformation is that it enables access to enantiopure enol silanes in a tautomerizing σ-bond metathesis, via deprotosilylation of ketones with allyl silanes as the silicon source. However, until today, this reaction has not been applied to racemic, 2-substituted, cyclic ketones. We show here that these important substrates readily undergo a highly enantioselective kinetic resolution furnishing the corresponding kinetically preferred enol silanes. Mechanistic studies suggest the fascinating possibility of advancing the process to a dynamic kinetic resolution.

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